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

HRID 1039032노트

반응식

HRID 1039032 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-3543d5515422496ba01160057b056898
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552032B2

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