Ammonia → (S)-tert-butyl 1-amino-3-cyclopropyl-1-oxopropan-2-ylcarbamate

HRID 624885노트

반응식

HRID 624885 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]1[CH2:16][CH2:15]1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.[N:32]1C=CC=CC=1.N>C(#N)C>[NH2:32][C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:13][CH:14]1[CH2:16][CH2:15]1

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 1049PyridineHCID 90495Di-tert-butyl dicarbonateHCID 5706350(S)-2-((tert-Butoxycarbonyl)amino)-3-cyclopropylpropanoic acid

생성물 1

HCID 70082562(S)-tert-butyl 1-amino-3-cyclopropyl-1-oxopropan-2-ylcarbamate수율 78%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of (S)-2-(tert-butoxycarbonylamino)-3-cyclopropylpropanoic acid (CAN 89483-06-7, 10 g, 44 mmol), di-tert-butyl dicarbonate (CAN:24424-99-5, 14.28 g, 66 mmol) and pyridine (2.4 mL) in acetonitrile (200 mL) was stirred at room temperature for 20 min. Ammonia (10 mL) was added dropwise for 20 min. The resulting reaction mixture was stirred for 4 h. During removal of most of the solvent under reduced pressure the product precipitated and the solid was filtered off and washed with acetonitrile (20 mL). The solid was dried under reduced pressure to give the title compound (7.73 g, 78%) as white solid; MS (EI): m/e 251.2 [M+Na]+.

후처리

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 4 h
  3. customDuring removal of most of the solvent under reduced pressure the product
  4. customprecipitated
  5. filtrationthe solid was filtered off
  6. washwashed with acetonitrile (20 mL)
  7. customThe solid was dried under reduced pressure

출처 및 근거

ORD 기록
ord-3d6210924cbb44549b69d168bacf4b68
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303012B2

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