Ethyl isocyanate → HCID 68726942, compound

HRID 2381025Notes

Reaction equation

HRID 2381025 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][C@H:8]([C:25](=[O:28])[NH:26][CH3:27])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:12]([OH:24])[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:30]([N:32]=[C:33]=[O:34])[CH3:31]>ClCCl.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:29])[NH:7][C@H:8]([C:25](=[O:28])[NH:26][CH3:27])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:12]([O:24][C:33](=[O:34])[NH:32][CH2:30][CH3:31])[CH:11]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 2

HCID 8022Ethyl isocyanateHCID 68744537HCID 68744537, compound

Product 1

HCID 68726942HCID 68726942, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

[(S)-2-(4-Benzyloxy-3-hydroxy-phenyl)-1-methylcarbamoyl-ethyl]-carbamic acid tert-butyl ester (348 mg) was dissolved in dry dichloromethane (2 ml) and ethyl isocyanate (0.31 ml) added followed by a catalytic amount of DMAP. The solution was heated at 50° C. for 5 hours and a white solid formed. The mixture was diluted with ethyl acetate and the crude product was filtered off and washed with ethyl acetate. Recrystallisation from methanol afforded [(S)-2-(4-benzyloxy-3-ethylcarbamoyloxy-phenyl)-1-methylcarbamoyl-ethyl]-carbamic acid tert-butyl ester, 253 mg; HPLC/MS Retention time 5.49 min, m/z 472 (MH+).

Workup

  1. customa white solid formed
  2. filtrationthe crude product was filtered off
  3. washwashed with ethyl acetate
  4. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-07ad628d99724e8f82a1a1ad5377ad9a
Source dataset
uspto-grants-2012_09
Patent number
US08258097B2

Reaction notes

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