Lawesson's reagent → tert-butyl (1R,3R,4S)-4-((benzyloxycarbonyl)amino)-3-carbamothioylcyclohexylcarbamate

HRID 2225311ノート

反応式

HRID 2225311 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:14][C@H:13]1[C:26](=O)[NH2:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:38])=CC=1>C1COCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:14][C@H:13]1[C:26](=[S:38])[NH2:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 87949Lawesson's reagentHCID 86596980tert-butyl (1R,3R,4S)-4-((benzyloxycarbonyl)amino)-3-carbamoylcyclohexylcarbamate

生成物 1

HCID 86596979tert-butyl (1R,3R,4S)-4-((benzyloxycarbonyl)amino)-3-carbamothioylcyclohexylcarbamate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of tert-butyl (1R,3R,4S)-4-((benzyloxycarbonyl)amino)-3-carbamoylcyclohexylcarbamate (4.8 g, 0.01 mol) in 50 ml of dry THF was added Lawesson's reagent (2.97 g, 0.007 mol) portionwise under nitrogen. After the completion of addition the reaction mixture was stirred for 5 h at RT. THF was removed and the crude product was dissolved in ethyl acetate. The organic layer was washed with 10% sodium hydroxide, water, brine and concentrated. The crude product was purified by recrystallization from pet-ether and ether mixture to give 3.5 g crude of tert-butyl (1R,3R,4S)-4-((benzyloxycarbonyl)amino)-3-carbamothioylcyclohexylcarbamate as a white solid.

後処理

  1. additionAfter the completion of addition the reaction mixture
  2. customTHF was removed
  3. dissolutionthe crude product was dissolved in ethyl acetate
  4. washThe organic layer was washed with 10% sodium hydroxide, water, brine
  5. concentrationconcentrated
  6. customThe crude product was purified by recrystallization from pet-ether and ether mixture

出典と根拠

ORDレコード
ord-e3f26a8005fb458a8e208813b711db2e
出典データセット
uspto-grants-2008_05
特許番号
US07378409B2

反応ノート

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