Dimethylamine, hydrochloride → Benzyl tert-butyl [(1S,2R,4S)-4-(dimethylcarbamoyl)cyclohexane-1,2-diyl]biscarbamate

HRID 459546ノート

反応式

HRID 459546 の反応式
[C:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[C@H:6]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:5]1)(O)=[O:2].Cl.[CH3:30][NH:31][CH3:32].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>ClCCl.O.C(N(CC)CC)C>[CH2:14]([O:13][C:11]([NH:10][C@H:7]1[CH2:8][CH2:9][C@H:4]([C:1](=[O:2])[N:31]([CH3:32])[CH3:30])[CH2:5][C@H:6]1[NH:21][C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

8

反応物 4

HCID 10473Dimethylamine, hydrochloride2 回HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 57416172(1S,3R,4S)-4-{[(Benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]cyclohexane-1-carboxylic acid

生成物 1

HCID 57416170Benzyl tert-butyl [(1S,2R,4S)-4-(dimethylcarbamoyl)cyclohexane-1,2-diyl]biscarbamate

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒2 回

実験手順

(1S,2R,4S)-4-Carboxy-N1-benzyloxycarbonyl-N2-(tert-butoxycarbonyl)-1,2-cyclohexanediamine was dissolved in dichloromethane (50 ml), and dimethylamine hydrochloride (240 mg), triethylamine (0.41 ml), 3-(3-dimethylaminopropyl)-1-ethylcarbodiimide hydrochloride (420 mg) and 1-hydroxybenzotriazole monohydrate (340 mg) were added to stir the mixture at room temperature for 1 hour. Dimethylamine hydrochloride (480 mg) and triethylamine (0.82 ml) were additionally added to the reaction mixture to stir the mixture at room temperature for additional 18 hours. The reaction mixture was poured into water to separate an organic layer. After the organic layer was washed with 1N hydrochloric acid and saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (methanol:methylene chloride=3:47→2:23) to obtain the title compound (620 mg) as a colorless foamy substance.

後処理

  1. stirringto stir the mixture at room temperature for additional 18 hours
  2. customto separate an organic layer
  3. washAfter the organic layer was washed with 1N hydrochloric acid and saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (methanol:methylene chloride=3:47→2:23)

出典と根拠

ORDレコード
ord-b3bb12ca48594850a44a7a04e4aa72a4
出典データセット
uspto-grants-2007_03
特許番号
US07192968B2

反応ノート

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