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

HRID 3141

反応式

HRID 3141 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-0a45a609ac2e45e08721ea94db9274b3
出典データセット
uspto-grants-1998_03
特許番号
US05733882

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