Phenyl isocyanate → HCID 131726906, compound

HRID 2225257Notes

Reaction equation

HRID 2225257 reaction equation
[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[CH2:26][OH:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:35]1([N:41]=[C:42]=[O:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>ClCCl.CN(C)C=O>[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]([CH3:22])([CH3:23])[CH3:24])[CH2:14][C@H:13]1[CH2:26][O:27][C:42](=[O:43])[NH:41][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7672Phenyl isocyanate2×HCID 8471TriethylamineHCID 68765914tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(hydroxymethyl)cyclohexylcarbamate

Product 1

HCID 131726906HCID 131726906, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl(1R,3R,4S)-4-benzyloxycarbonylamino-3-(hydroxymethyl)cyclohexylcarbamate (75 mg) in dichloromethane (1 mL) and N,N-dimethylformamide (0.1 mL) was-treated with triethylamine (3 μL) and phenyl isocyanate (33 μL), and the mixture was and stirred at rt for 18 h. Additional phenyl isocyanate (22 μL) was added and stirring was continued for 96 h. The mixture was concentrated, and the residue was purified by flash column chromatography on silica gel, eluting with 4:6 v/v ethyl acetate/hexane, to provide tert-butyl(1R,3R,4S)-(4-benzyloxycarbonylamino-3-phenylcarbamoyloxymethylcyclohexyl)carbamate as a white glassy foam (85 mg). MS found: (M+H)+=498.3.

Workup

  1. stirringstirring
  2. waitwas continued for 96 h
  3. concentrationThe mixture was concentrated
  4. customthe residue was purified by flash column chromatography on silica gel
  5. washeluting with 4:6 v/v ethyl acetate/hexane

Sources & evidence

ORD record
ord-82ef39793afe4e9eb8cad0c739d19aa3
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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