N-(tert-Butoxycarbonyl)-L-alanine

English name

N-(tert-Butoxycarbonyl)-L-alanine

English synonyms

BOC-L-ALANINE;BOC-L-ALANINE-OH;BOC-L-ALA-OH;BOC-L-ALA;BOC-ALA;BOC-ALANINE;BOC-ALA-OH;H-ALPHA-T-BOC-L-ALANINE

CAS number

15761-38-3

Molecular formula

C8H15NO4

Molecular weight

189.21

EINECS

239-847-8

Related Categories

Boc-protected amino acids; protected amino acids and peptide products; amino acids; amino acids; amino acids and derivatives; pharmaceutical raw materials; biochemical reagents - amino acids; organic raw materials; traditional Chinese medicine reference substances; chemical reagents; Boc-amino acids; amino acids; amino acids and their derivatives; intermediates; chemical biology; standard substances; Boc-protected amino acids; other biochemical reagents; pharmaceutical intermediates; amino acid derivatives Biology; Protected Amino Acids; Raw Materials; Biochemical Reagents - Amino Acids; Chemical Raw Materials; Chemical Industry; Organic Chemical Raw Materials; General Biochemical Reagents - Amino Acids; Protected Amino Acid Series - BOC Protected Amino Acids; Chemical Reagents; Reference Materials; PrChemical Books; Protected Amino Acids; Straight Chain Compounds; Amino Acids; Amino Acid Derivatives; Protected Aminoacids & Peptides; Alanine [Ala, A]; Boc-Amino Acids and Derivatives; Amino Acids (N-Protected); Biochemistry; Boc-Aminoacid series; Naphthyridines

Mol file

15761-38-3.mol

Melting Point

79-83 °C (lit.)

Specific Rotation

-26°C (C=2, acetic acid)

Boiling Point

324.46°C (rough estimate)

Density

1.2321°C (rough estimate)

Refractive Index

-25.5°C (C=2, AcOH)

Storage Conditions

Sealed in dry, 2-8°C

Solubility

Soluble in dimethyl sulfoxide and methanol

PKa

4.02±0.10 (Predicted)

Form

Granular powder

Color

White

Optical Rotation

[Pseudo]20/D 25% halogen, C = 2% in acetic acid acid

BRN

1726365

InChI

InChI=1S/C8H15NO4/c1-5(6(10)11)9-7(12)13-8(2,3)4/h5H,1-4H3,(H,9,12)(H,10,11)/t5-/m0/s1

InChIKey

QVHJQCGUWFKTSE-YFKPBYRVSA-N

SMILES

C(O)(=O)[C@H](C)NC(OC(C)(C)C)=O

CAS Database

15761-38-3(CAS DataBase Reference)

EPA Chemical Substance Information

L-Alanine, N-[(1,1-dimethylethoxy)carbonyl]- (15761-38-3)

Appearance

It is a white solid at room temperature and pressure.

Applications

N-tert-Butyloxycarbonyl-L-alanine is an amino acid derivative widely used in the preparation and synthesis of peptide drug molecules and bioactive molecules. It is also a synthetic intermediate for biomacromolecules such as proteins and is widely used in the production of fine chemicals in biochemistry, food, cosmetics, and other fields.

Synthesis Method

To a suspension of S-alanine (1.0 equivalent) in a 1:1 mixture of dioxane and water (100 mL) was added with stirring at room temperature a 2N aqueous sodium hydroxide solution. The resulting reaction mixture was transferred to an ice-water bath, cooled to 0°C, and stirred for 15 minutes. A solution of (Boc)2O (1.1 equivalent) in dioxane (10 mL) was then added to the reaction mixture. The resulting reaction mixture was stirred at 0°C for 45 minutes. The ice bath was removed and the reaction mixture was warmed to room temperature. The completion of the reaction was monitored by TLC. After the reaction, the reaction mixture is concentrated under reduced pressure. The aqueous layer is then acidified with citric acid (pH 2-3), and the mixture is extracted three times with ethyl acetate. All organic layers are combined and washed three times with brine. The organic layer is separated and dried over Na₂SO₄. The desiccant is filtered to remove the filtrate, and the resulting filtrate is concentrated under reduced pressure to yield N-tert-butyloxycarbonyl-L-alanine.

Uses

This product is used in the synthesis of proteins and peptides, and is widely used in the synthesis of various products, including pharmaceuticals, biochemistry, food, and cosmetics.

Uses

It is used in the synthesis of biochemical reagents and peptides.

Hazardous material symbol

Xi,Xn

Hazard category code

20/21/22-36/37/38

Safety instructions

24/25-36-26

WGK Germany

3

TSCA

Yes

Customs code

2924 19 00

Hazard level

IRRITANT

Upstream raw materials

4-Hydroxythiophenol BOC-L-alanine tert-butyl ester BOC-L-alanine methyl ester tert-butyl alcohol L-alanine tert-butyl azidoformate

Downstream products

Cyclo(alanyl-alanyl) 1-BOC-acetamide (S)-4-methyloxazolidine-2,5-dione Carbamicacid, N-[(1S)-2-(3-methoxyphenyl)-1-methyl-2-oxoethyl]-,1,Chemicalbook1-dimethylethylester, N-[(1S)-1-methyl-2-(6-nitro-1H-benzotriazol-1-yl)-2-thioneethyl]carbamic acid tert-butyl ester (1-((methoxymethyl)amino)-1-oxopropan-2-yl)carbamic acid tert-butyl ester