Boc-o-methyl-D-serine Chemical Properties

Boiling point:

355.8±37.0 °C(Predicted)

Density 

1.148±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

3.52±0.10(Predicted)

Appearance

White to light yellow Solid

optical activity

Consistent with structure

InChI

InChI=1S/C9H17NO5/c1-9(2,3)15-8(13)10-6(5-14-4)7(11)12/h6H,5H2,1-4H3,(H,10,13)(H,11,12)/t6-/m1/s1

InChIKey

RFGMSGRWQUMJIR-ZCFIWIBFSA-N

SMILES

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

Safety Information

HS Code 

2924190090

Boc-o-methyl-D-serine Usage And Synthesis

Uses

Boc-O-methyl-D-serine is used in preparation of acylamino acid heterocyclyl amides and deuterated derivatives for the treatment of BAF complex-related disorders.

Synthesis

The general procedure for the synthesis of (R)-2-tert-butoxycarbonylamino-3-methoxypropionic acid from BOC-L-serine and dimethyl sulfate was as follows: N-Boc-L-serine (22 g, 0.107 mol) was dissolved in anhydrous tetrahydrofuran (352 ml), the solution was cooled down to 0°C and the reaction mixture was stirred for 9 hours at 0-5°C. Upon completion of the reaction, the reaction was quenched by the addition of water (110 ml) and the pH was adjusted to 10-13 with 30% sodium hydroxide solution (3 ml). subsequently, the tetrahydrofuran/hexane mixture was removed by vacuum evaporation. The residue was washed with toluene (44 ml) and then acidified with 50% citric acid solution to pH < 3.5. The acidified aqueous phase was extracted with dichloromethane (2 x 91 ml, 1 x 66 ml) and the combined dichloromethane extracts were dried by azeotropic distillation. Eventually, evaporation of the solvent gave 23.7 g of product in 100% yield. The product was analyzed by HPLC showing 90.0% purity and 100% chiral purity.

References

[1] Patent: WO2006/37574, 2006, A1. Location in patent: Page/Page column 17
[2] Patent: WO2006/37574, 2006, A1. Location in patent: Page/Page column 17-18
[3] Patent: CN104030943, 2016, B. Location in patent: Paragraph 0103; 0104
[4] Patent: WO2012/51551, 2012, A1. Location in patent: Page/Page column 36-37
[5] Tetrahedron, 2010, vol. 66, # 29, p. 5384 - 5395

Boc-o-methyl-D-serine(86123-95-7)Related Product Information

• BOC-D-TYR(BZL)-OH
• Boc-D-Serine
• Boc-O-Benzyl-D-threoninol
• Boc-o-methyl-D-serine
• DIMETHYL (BOC-AMINO)MALONATE
• N-BOC-O-Benzyl-L-serine
• DIETHYL (BOC-AMINO)MALONATE
• 4-Boc-3(R)-morpholinecarboxylic acid
• N-(tert-Butoxycarbonyl)-O-benzyl-D-threonine
• BOC-D-SER(BZL)-OSU
• METHYL (R)-(+)-3-(TERT-BUTOXYCARBONYL)-2,2-DIMETHYL-4-OXAZOLIDINECARBOXYLATE
• (R)-2,2-DIMETHYL-OXAZOLIDINE-3,4-DICARBOXYLIC ACID 3-TERT-BUTYL ESTER
• BOC-(2R,3R)-2-AMINO-3-ETHOXYBUTANOIC ACID
• 4-Methyl 2-Tert-Butyloxazolidine-3,4-Dicarboxylate
• Boc-D-Ser(tBu)-OH
• BOC-D-THR(TBU)-OH
• BOC-(2R,3R)-2-AMINO-3-METHYLOXYBUTANOIC ACID
• BOC-D-MESER(ME)-OH