| Identification | Back Directory | [Name]
D-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-methyl- (9CI) | [CAS]
86123-95-7 | [Synonyms]
Boc-D-Ser(Me)-OH
BOC-O-METHYL-D-SERINE
Boc-N-D-O-methylserine
N-Boc-(D)-O-Methylserine
Boc-O-Methyl-D-serine 97%
N-Boc-O-Methyl-D-serine, 98%
(R)-N-Boc-2-aMino-3-Methoxypropionic acid
2-(tert-butoxycarbonylamino)-3-methoxypropanoic acid
D-Serine, N-[(1,1-diMethylethoxy)carbonyl]-O-Methyl-
(R)-2-(tert-Butoxycarbonylamino)-3-methoxypropionic acid
O-Methyl-N-{[(2-Methyl-2-propanyl)oxy]carbonyl}-D-serine
D-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-methyl- (9CI)
(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxypropanoic acid | [EINECS(EC#)]
1308068-626-2 | [Molecular Formula]
C9H17NO5 | [MDL Number]
MFCD08063987 | [MOL File]
86123-95-7.mol | [Molecular Weight]
219.235 |
| Chemical Properties | Back Directory | [Boiling point ]
355.8±37.0 °C(Predicted) | [density ]
1.148±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [pka]
3.52±0.10(Predicted) | [Appearance]
White to light yellow Solid | [Optical Rotation]
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 |
| Hazard Information | Back Directory | [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 |
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