Acetic Acid → tert-butyl N-[(2S)-1-{[(tert-butoxy)carbonyl]amino}-3-hydroxypropan-2-yl]carbamate

HRID 1994125노트

반응식

HRID 1994125 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 86606496tert-butyl N-[(2S)-1-{[(tert-butoxy)carbonyl]amino}-3-hydroxypropan-2-yl]carbamate수율 72.3%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-1c06efc9f3db4ec1a0d2f702ec34232f
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652041B2

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