Hydrazine → (S)-tert-butoxycarbonylamino-3-thiocarbamoyl-propionic acid benzyl ester

HRID 1039032ノート

反応式

HRID 1039032 の反応式
[NH2:1][C:2](=O)[CH2:3][C@H:4]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1.NN>O1CCCC1>[CH2:8]([O:7][C:5](=[O:6])[C@@H:4]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:3][C:2](=[S:33])[NH2:1])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

5

反応物 3

HCID 9321HydrazineHCID 87949Lawesson's reagentHCID 14420402Benzyl N~2~-(tert-butoxycarbonyl)-L-asparaginate

生成物 1

HCID 86654757(S)-tert-butoxycarbonylamino-3-thiocarbamoyl-propionic acid benzyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A 1-L round bottom flask was charged with (S)-benzyl 4-amino-2-(tert-butoxycarbonylamino)-4-oxobutanoate (10.0 g, 31.0 mmol), Lawesson's reagent (6.58 g, 16.3 mmol), and tetrahydrofuran (155 mL). Hydrazine (7.8 mL, 0.248 mol) was added and the resulting mixture was stirred at room temperature for 72 h. The resulting mixture was then concentrated in vacuo and the residue purified via flash silica gel chromatography (Analogix IF-280, SF40-400 g column, gradient 90:10-60:40 Heptane:EtOAc) to yield-(S)-tert-butoxycarbonylamino-3-thiocarbamoyl-propionic acid benzyl ester. MS (ES+) 339 (M+1).

後処理

  1. concentrationThe resulting mixture was then concentrated in vacuo
  2. customthe residue purified via flash silica gel chromatography (Analogix IF-280

出典と根拠

ORDレコード
ord-3543d5515422496ba01160057b056898
出典データセット
uspto-grants-2013_10
特許番号
US08552032B2

反応ノート

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