Imidazole → methyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-[(tert-butyldiphenylsilyl)oxy]propanoate

HRID 1711196Notes

Reaction equation

HRID 1711196 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C@H:4]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5][OH:6].N1C=CN=C1.[Si:21](Cl)([C:34]([CH3:37])([CH3:36])[CH3:35])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH3:1][O:2][C:3](=[O:15])[C@H:4]([NH:7][C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[CH2:5][O:6][Si:21]([C:34]([CH3:37])([CH3:36])[CH3:35])([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 377723N-Boc-D-serine methyl ester

Product 1

HCID 11762248methyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-[(tert-butyldiphenylsilyl)oxy]propanoateYield 72.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-2-tert-Butoxycarbonylamino-3-hydroxy-propionic acid methyl ester (2.2 mg, 10 mmol) was dissolved in THF (20 ml). Imidazole (818 mg, 12 mmol) and TBDPS chloride (2.9 ml, 11 mmol) were added. The mixture was stirred at rt overnight. The mixture was then partitioned between CH2Cl2 and water (30 ml/30 ml). The organic layer was concentrated and the residue was purified by column chromatography (6/1, Hexanes/EtOAc) to give (R)-2-tert-butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid methyl ester (3.3 g, 72%).

Workup

  1. customThe mixture was then partitioned between CH2Cl2 and water (30 ml/30 ml)
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by column chromatography (6/1, Hexanes/EtOAc)

Sources & evidence

ORD record
ord-c430f316576c46f58d1614a10a8bcfcf
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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