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

HRID 233339

반응식

HRID 233339 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].Cl[Si](C)(C)C.Br[CH2:31][Cl:32].Cl>CCCCCC.O1CCCC1.O>[CH2:18]([C@H:13]([NH:12][C:10](=[O:11])[O:9][CH3:8])[C:14](=[O:16])[CH2:31][Cl:32])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 6333BromochloromethaneHCID 6397ChlorotrimethylsilaneHCID 10609905(S)-Methyl 2-((methoxycarbonyl)amino)-3-phenylpropanoateHCID 178506865HCID 178506865, 화합물2회

생성물 1

HCID 9881533methyl (S)-(1-benzyl-3-chloro-2-oxo-propyl)carbamate수율 70%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

15.4 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 in 60 ml of tetrahydrofuran. Subsequently, the mixture was treated with 5.60 ml of chlorotrimethylsilane. The resulting suspension was stirred and treated with 3.22 ml of bromochloromethane. Subsequently, 18.4 ml of hexyllithium solution were added. The solution was treated at -80° C. with 11 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 and the organic phase was washed with saturated sodium chloride solution, dried and concentrated. The residue was recrystallized from ethyl acetate and hexane and the crystallizate was dried, there being obtained 7.20 g (70%) of pure methyl (S)-(1-benzyl-3-chloro-2-oxo-propyl)-carbamate, m.p. 122°-123° 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 ethyl acetate and hexane
  7. customthe crystallizate was dried

출처 및 근거

ORD 기록
ord-9bef9ffaabdf42c7983198d7d20b557d
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05591885

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