BOC-D-ALA-OME Chemical Properties

Melting point:

34-37 °C(lit.)

Boiling point:

341.54°C (rough estimate)

Density 

1.03 g/mL at 25 °C(lit.)

refractive index 

1.4315 (estimate)

Flash point:

>230 °F

storage temp. 

2-8°C

form 

Powder

pka

11.21±0.46(Predicted)

color 

White

optical activity

[α]20/D +45°, c = 1 in methanol

BRN 

4310313

InChI

InChI=1S/C9H17NO4/c1-6(7(11)13-5)10-8(12)14-9(2,3)4/h6H,1-5H3,(H,10,12)/t6-/m1/s1

InChIKey

GJDICGOCZGRDFM-ZCFIWIBFSA-N

SMILES

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

Safety Information

WGK Germany 

3

HS Code 

2924297099

MSDS

• Language:English Provider:SigmaAldrich

BOC-D-ALA-OME Usage And Synthesis

Chemical Properties

White powder

Uses

peptide synthesis

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

General procedure for the synthesis of Boc-D-alanine methyl ester from di-tert-butyl dicarbonate and D-alanine methyl ester hydrochloride: di-tert-butyl dicarbonate (11.7 g, 53.7 mmol) was added to an aqueous solution (100 mL) containing D-alanine methyl ester hydrochloride (5 g, 35.8 mmol) and sodium hydrogen carbonate (9.0 g, 107 mmol). The reaction mixture was stirred at room temperature. Upon completion of the reaction, the reaction mixture was extracted with dichloromethane (DCM, 3 x 100 mL), the organic phases were combined and dried over anhydrous magnesium sulfate (MgSO4). The dried organic phase was filtered and concentrated under reduced pressure. Nuclear magnetic resonance (NMR) analysis of the crude product showed the presence of a large amount of unreacted di-tert-butyl dicarbonate. Therefore, the crude product was dissolved in dichloromethane (DCM, 50 mL), treated with N,N-dimethylethylenediamine (5 mL) and stirred for 30 min. Subsequently, the solution was washed with 1 M hydrochloric acid (HCl, 50 mL), and the organic phase was again dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to give 5.35 g of Boc-D-alanine methyl ester in 73% yield as a colorless liquid.1H NMR (500 MHz, chloroform-d) δ 5.04 (s,1H), 4.31 (m,1H), 3.73 (s,3H), 1.44 (s,9H), 1.37 (d,J=7.2Hz,3H).

References

[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 2299 - 2306
[2] Patent: WO2016/91776, 2016, A1. Location in patent: Page/Page column 387
[3] Heterocycles, 1988, vol. 27, # 9, p. 2077 - 2080
[4] Journal of Organic Chemistry, 1998, vol. 63, # 1, p. 92 - 98
[5] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 4, p. 387 - 398

BOC-D-ALA-OME(91103-47-8)Related Product Information

• tert-Butoxytrimethylsilane
• BOC-L-Proline
• Boc-L-Glutamic acid 1-benzyl ester
• BOC-GLN-ONP
• BOC-D-SER-OME
• BOC-3-IODO-D-ALANINE METHYL ESTER
• BOC-D-PHENYLALANINE 4-NITROPHENYL ESTER
• BOC-D-ALA-OME
• BOC-D-PRO-OME
• DIETHYL (BOC-AMINO)MALONATE
• (L)-BOC-PHENYL-ALANINE METHYL ESTER
• 3-AMINO-N-BOC-L-ALANINE METHYL ESTER
• BOC-D-Alanine
• BOC-D-ASN-ONP
• BOC-3-IODO-D-ALANINE BENZYL ESTER
• BOC-D-GLU(OTBU)-ONP
• BOC-D-ASP-OTBU
• BOC-D-TYR-OME