Lawesson's reagent → 1,1-Dimethylethyl N-[(1S)-1-(aminothioxomethyl)-2-methylpropyl]carbamate

HRID 3141

반응식

HRID 3141 반응식
[C:1]([NH:8][C@H:9]([C:13]([NH2:15])=O)[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:25])=CC=1>C1COCC1>[C:1]([NH:8][C@H:9]([C:13](=[S:25])[NH2:15])[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

참가 물질

4

반응물 2

HCID 87949Lawesson's reagentHCID 11241393Boc-L-valine amide

생성물 1

HCID 110207761,1-Dimethylethyl N-[(1S)-1-(aminothioxomethyl)-2-methylpropyl]carbamate수율 70%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Boc-valineamide (0.5 g) was stirred in dry THF at room temperature under argon. Lawesson's reagent (1.56 g, 0.6 eq) was added and the mixture was stirred overnight. The solvent was evaporated and the residue chromatographed (silica, 2.5% methanol/dichloromethane) to give the title compound as a white solid (0.373 g, 70%). NMR(CDCl3) δ 8.59 (1H, br s), 8.09 (1H, br s), 5.41 (1H, d (br)), 4.20 (1H, dd), 1.99 (1H, m), 1.39 (9H, s), 0.90 (6H, m).

후처리

  1. customThe solvent was evaporated
  2. customthe residue chromatographed (silica, 2.5% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-0a45a609ac2e45e08721ea94db9274b3
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733882

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