Acetic Acid → 471296-73-8

HRID 1994125Notes

Reaction equation

HRID 1994125 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[Li+].[BH4-].[Na+].C(O)(=O)C>C1COCC1.C(O)C>[OH:11][CH2:10][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:14][NH:15][C:16](=[O:17])[O:18][C:19]([CH3:21])([CH3:22])[CH3:20]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 86606495HCID 86606495, compound

Product 1

HCID 86606496471296-73-8Yield 72.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (2S)-2,3-bis[(tert-butoxycarbonyl)amino]-propanoate (3.57 g, 11.2 mmol) in THF (60 mL) at 0° C. was added lithium chloride (523 mg, 12.3 mmol) and then sodium borohydride (467 mg, 12.3 mmol) portionwise. Ethanol (30 mL) was added slowly. The reaction mixture was allowed to warm to rt and stirred for 18 h. Acetic acid (0.707 mL, 12.3 mmol) was added and the solvents were evaporated. The residue was purified by chromatography (SiO2, EtOAc/hexane) to yield the title compound as a white solid (2.35 g, 72.2%). LCMS: (FA) ES+ 291.2 (M+1).

Workup

  1. customthe solvents were evaporated
  2. customThe residue was purified by chromatography (SiO2, EtOAc/hexane)

Sources & evidence

ORD record
ord-1c06efc9f3db4ec1a0d2f702ec34232f
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

Loading…