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

HRID 233339

反応式

HRID 233339 の反応式
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

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 6333BromochloromethaneHCID 6397ChlorotrimethylsilaneHCID 10609905(S)-Methyl 2-((methoxycarbonyl)amino)-3-phenylpropanoateHCID 178506865HCID 178506865、化合物2 回

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9bef9ffaabdf42c7983198d7d20b557d
出典データセット
uspto-grants-1997_01
特許番号
US05591885

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