BOC-SAR-OH Chemical Properties

Melting point:

88-90 °C

Boiling point:

324.46°C (rough estimate)

Density 

1.2321 (rough estimate)

refractive index 

1.4540 (estimate)

storage temp. 

2-8°C

solubility 

Chloroform (Sparingly), DMSO (Sparingly), Methanol (Slightly)

form 

Crystals or Crystalline Powder

pka

4.03±0.10(Predicted)

color 

White

BRN 

2046827

Stability:

Hygroscopic

InChI

InChI=1S/C8H15NO4/c1-8(2,3)13-7(12)9(4)5-6(10)11/h5H2,1-4H3,(H,10,11)

InChIKey

YRXIMPFOTQVOHG-UHFFFAOYSA-N

SMILES

C(O)(=O)CN(C(OC(C)(C)C)=O)C

CAS DataBase Reference

13734-36-6(CAS DataBase Reference)

EPA Substance Registry System

Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl- (13734-36-6)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

F 

21

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29241990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

BOC-SAR-OH Usage And Synthesis

Chemical Properties

white crystals or crystalline powder

Uses

Boc-N-methylglycine is used in the preparation of Clavatustide A (C563723) and Clavatustide B (C563725), which have been shown to suppress the proliferation of human hepatocellular carcinoma cells under specific conditions.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

Triethylamine (23.5 mL, 168.3 mmol) and di-tert-butyl dicarbonate (12.9 mL, 56.1 mmol) were sequentially added to an aqueous (375 mL) solution of sarcosine (5.0 g, 56.1 mmol), and the reaction mixture was stirred for 6 hours at room temperature. After completion of the reaction, hydrochloric acid solution (320 mL, 1 M aqueous solution) and ethyl acetate were added for acidification and extraction. After separation of the aqueous layer, the aqueous layer was further extracted with ethyl acetate. The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a colorless oil. The oily substance was crystallized at -15 °C to afford the target product 2-((tert-butoxycarbonyl)(methyl)amino)acetic acid (10.6 g, quantitative yield) as a white solid and a mixture of rotary isomers was observed.

References

[1] Tetrahedron Letters, 2017, vol. 58, # 7, p. 602 - 605
[2] Journal of the American Chemical Society, 2003, vol. 125, # 35, p. 10664 - 10671
[3] Synthesis, 1996, # 10, p. 1246 - 1258
[4] Patent: WO2005/39506, 2005, A2. Location in patent: Page/Page column 93-94
[5] Patent: WO2005/39506, 2005, A2. Location in patent: Page/Page column 93-94

BOC-SAR-OH(13734-36-6)Related Product Information

• BOC-ORN-OH
• Boc-N-beta-Trityl-L-asparagine
• N-tert-Butoxycarbonyl-L-glutamic acid gamma-tert-butyl ester
• Boc-L-aspartic acid 4-tert-butyl ester
• Boc-6-AMinocaproic acid
• BOC-NLE-OH DCHA
• Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate
• Boc-L-glutamic acid 5-cyclohexyl ester
• Boc-D-aspartic acid 4-benzyl ester
• BOC-GLU(OFM)-OH
• BOC-PHE-SER-ARG-AMC ACETATE SALT
• BOC-4-IODO-L-PHENYLALANINE
• Boc-N-methyl-L-leucine
• BOC-D-MEPHE-OH DCHA
• N-tert-Butyloxycarbonyl-N-methyl-O-benzyl-L-threonine
• BOC-N-Methyl-L-alanine
• BOC-HYP(BZL)-OH
• Sarcosine