Hydrochloric Acid → methyl (S)-(1-benzyl-3-chloro-2-oxo-propyl)carbamate

HRID 233338

반응식

HRID 233338 반응식
C([Li])CCCCC.[CH3:8][O:9][C:10]([NH:12][C@@H:13]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:14]([O:16]C)=O)=[O:11].Br[CH2:26][Cl:27].Cl>CCCCCC.O1CCCC1.O>[CH2:18]([C@H:13]([NH:12][C:10](=[O:11])[O:9][CH3:8])[C:14](=[O:16])[CH2:26][Cl:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 6333Bromochloromethane3회HCID 10609905(S)-Methyl 2-((methoxycarbonyl)amino)-3-phenylpropanoateHCID 178506865HCID 178506865, 화합물3회

생성물 1

HCID 9881533methyl (S)-(1-benzyl-3-chloro-2-oxo-propyl)carbamate수율 37%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

41.7 ml of a 2.6 molar solution of hexyllithium in hexane were added dropwise at -80° C. to a solution of 9.50 g of methyl (S)-2-methoxycarbonylamino-3-phenyl-propionate and 3.22 ml of bromochloromethane in 60 ml of tetrahydrofuran. Subsequently, a further 2.14 ml of bromochloromethane were added and the mixture was again treated with 23 ml of hexyllithium solution, a further 1.54 ml of bromochloromethane were added and the mixture was again treated with 7.7 ml of hexyllithium solution. The solution was treated at -80° C. with 15 ml of 20% methanolic hydrochloric acid, warmed to 22° and diluted with 100 ml of water and 40 ml of tetrahydrofuran. The phases were separated, the organic phase was washed with saturated sodium chloride solution, dried and concentrated. The residue was recrystallized from 40 ml of ethyl acetate and 160 ml of hexane and the crystallizate was dried, there being obtained 3.83 g (37%) of pure methyl (S)-(1-benzyl-3-chloro-2-oxo-propyl)-carbamate, m.p. 121°-122° C. IR (KBr): 3336s (NH), 1737s and 1686s (C=O), 1535s (amide II).

후처리

  1. temperaturewarmed to 22°
  2. customThe phases were separated
  3. washthe organic phase was washed with saturated sodium chloride solution
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was recrystallized from 40 ml of ethyl acetate and 160 ml of hexane
  7. customthe crystallizate was dried

출처 및 근거

ORD 기록
ord-769171b329f44205846c3f76086df0b3
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05591885

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