Phenyl isocyanate → HCID 67243902, compound

HRID 2425443Notes

Reaction equation

HRID 2425443 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C@H:6]1[CH2:10][CH2:9][N:8]([S:11]([C:14]2[C:15]3[C:16]([CH3:24])=[CH:17][N:18]=[CH:19][C:20]=3[CH:21]=[CH:22][CH:23]=2)(=[O:13])=[O:12])[CH2:7]1.C(N(CC)CC)C.[C:32]1([N:38]=[C:39]=[O:40])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(=O)([O-])O.[Na+]>ClCCCl>[CH3:24][C:16]1[C:15]2[C:14]([S:11]([N:8]3[CH2:9][CH2:10][C@H:6]([NH:5][CH2:4][CH2:3][CH2:2][NH:1][C:39]([NH:38][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[O:40])[CH2:7]3)(=[O:13])=[O:12])=[CH:23][CH:22]=[CH:21][C:20]=2[CH:19]=[N:18][CH:17]=1

Participants

6

Reactant 4

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 67244631HCID 67244631, compound

Product 1

HCID 67243902HCID 67243902, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A suspension of Intermediate 40a (75 mg) obtained in Step A in 1,2-dichloroethane (3 ml) was cooled on ice, and added with triethylamine (114 μl) and phenyl isocyanate (21 μl, Tokyo Kasei Kogyo), and the mixture was stirred for 1 hour, and then further stirred at room temperature for 10 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate (5 ml), and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (chloroform:methanol=15:1) to obtain the title compound (33 mg).

Workup

  1. temperaturewas cooled on ice
  2. stirringfurther stirred at room temperature for 10 hours
  3. customthe organic layer was separated
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-ef29a877407046b3a15cddf87e6f2b1c
Source dataset
uspto-grants-2011_06
Patent number
US07964613B2

Reaction notes

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