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

HRID 459546노트

반응식

HRID 459546 반응식
[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

참가 물질

8

반응물 4

HCID 10473Dimethylamine, hydrochloride2회HCID 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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8471Triethylamine용매2회

실험 절차

(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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b3bb12ca48594850a44a7a04e4aa72a4
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192968B2

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