Methyl Isocyanate → HCID 86596172, compound

HRID 1271104Notes

Reaction equation

HRID 1271104 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH2:15][C@H:14]3[N:11]([C:12](=[O:26])[C@@H:13]3[C@H:16]([O:18][Si:19]([CH2:24][CH3:25])([CH2:22][CH3:23])[CH2:20][CH3:21])[CH3:17])[C:10]=2[C:27]([O:29][CH2:30][CH:31]=[CH2:32])=[O:28])[CH:6]=[CH:7][CH:8]=1.C(N(CC)C(C)C)(C)C.[CH3:42][N:43]=[C:44]=[O:45]>ClCCl>[CH3:42][NH:43][C:44]([O:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH2:15][C@H:14]3[N:11]([C:12](=[O:26])[C@@H:13]3[C@H:16]([O:18][Si:19]([CH2:20][CH3:21])([CH2:24][CH3:25])[CH2:22][CH3:23])[CH3:17])[C:10]=2[C:27]([O:29][CH2:30][CH:31]=[CH2:32])=[O:28])[CH:6]=[CH:7][CH:8]=1)=[O:45]

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 81531DiisopropylethylamineHCID 86596171HCID 86596171, compound

Product 1

HCID 86596172HCID 86596172, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Allyl (5R,6S)-3-[3-(hydroxymethyl)phenyl]-7-oxo-6-{(1R)-1-[(triethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (250 mg) prepared in the above step, was dissolved in dichloromethane (10 ml), and thereto were added N,N-diisopropylethylamine (14 mg) and methyl isocyanate (276 mg). The mixture was stirred for 1 day, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform) to give allyl (5R,6S)-3-[3-({[(methylamino)carbonyl]oxy}methyl)phenyl]-7-oxo-6-{(1R)-1-[(triethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (122 mg).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-9e8cb7e726a24b888996169a83eb63ac
Source dataset
uspto-grants-2007_04
Patent number
US07205291B2

Reaction notes

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