Benzyl isocyanate → HCID 57220037, compound

HRID 1384722Notes

Reaction equation

HRID 1384722 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][CH2:8][C@H:7]([NH:16][C:17]([O:19]C(C)(C)C)=O)[C:6]1=[O:24].[CH2:26]([N:33]=[C:34]=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl.CN(C=O)C>[CH3:1][O:2][C:3](=[O:25])[CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([C:34]([NH:33][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:35])[CH2:8][C@H:7]([NH:16][C:17](=[O:19])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]1=[O:24]

Participants

5

Reactant 2

HCID 76639Benzyl isocyanateHCID 54305289(3S)-2-Oxo-3-tert-butoxycarbonylamino-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl ester

Product 1

HCID 57220037HCID 57220037, compoundYield 164.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 600a/103 (400 mg, 1.1 mmol) and benzylisocyanate (166 mg, 1.2mmol) in 10 ml of CH2Cl2 and 10 ml of DMF and heated at 80° C. for 3 days. The reaction was cooled to RT poured onto H2O and extracted with EtOAc (2×). The combined organic layers were washed with H2O (4×) and sat. aq. NaCl, dried over MgSO4 and concentrated in vacuo. Chromatography (flash, SiO2, 50% to 80% EtOAc/hexane) gave 440 mg (80%) of 602p as a white solid.

Workup

  1. additionpoured onto H2O
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with H2O (4×) and sat. aq. NaCl
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6522348609214051a457bc8d95130252
Source dataset
uspto-grants-2001_07
Patent number
US06258948B1

Reaction notes

Loading…