Benzyl chloroformate → (S)-2-Benzyloxycarbonylamino-3-(4-hydroxy-phenyl)-2-methyl-propionic acid methyl ester

HRID 13581

反応式

HRID 13581 の反応式
Cl.[CH3:2][O:3][C:4](=[O:16])[C@:5]([NH2:15])([CH3:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.C([O-])(O)=O.[Na+].Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>C(OCC)(=O)C>[CH3:2][O:3][C:4](=[O:16])[C@:5]([NH:15][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])([CH3:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1

参加物

5

反応物 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 24847455(S)-Methyl 2-amino-3-(4-hydroxyphenyl)-2-methylpropanoate hydrochloride

生成物 1

HCID 66719336(S)-2-Benzyloxycarbonylamino-3-(4-hydroxy-phenyl)-2-methyl-propionic acid methyl ester

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of (S)-2-amino-3-(4-hydroxy-phenyl)-2-methyl-propionic acid methyl ester hydrochloride in ethyl acetate (25 mL) was added 1N NaHCO3 solution (12.5 ml.) and the mixture was stirred rapidly at ambient temperature for the addition of neat benzyl chloroformate (0.859 g, 1.01 eq., 5.05 mmol). Following addition, the reaction mixture was stirred for an additional hour; TLC and LC-MS analysis showed the reaction to be complete. The mixture was partitioned and the organic phase was separated and dried over Na2SO4 and concentrated. The crude product was used directly in the subsequent reaction without purification.

後処理

  1. additionaddition
  2. customthe reaction
  3. customThe mixture was partitioned
  4. customthe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was used directly in the subsequent reaction without purification

出典と根拠

ORDレコード
ord-453b935c31c044258a78e94583fc8b0d
出典データセット
uspto-grants-2010_06
特許番号
US07727983B2

関連ノート

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