tert-Butyl isocyanate → HCID 86597661, compound

HRID 350751Notes

Reaction equation

HRID 350751 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:14][CH2:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][P:26]([O:31][CH2:32][CH3:33])([O:28][CH2:29][CH3:30])=[O:27])=[CH:21][CH:20]=2)=[O:17])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.[C:34]([N:38]=[C:39]=[O:40])([CH3:37])([CH3:36])[CH3:35]>C1(C)C=CC=CC=1>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[N:6]=[C:2]([NH:1][C:39]([NH:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:40])[S:3][C:4]=2[CH2:14][CH2:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][P:26]([O:28][CH2:29][CH3:30])([O:31][CH2:32][CH3:33])=[O:27])=[CH:21][CH:20]=2)=[O:17])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 86597659HCID 86597659, compound

Product 1

HCID 86597661HCID 86597661, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-[2-amino-4-(4-chlorophenyl)-5-thiazolyl)-N-[4-(diethylphosphonomethyl)phenyl]propionamide (400 mg), tert-butyl isocyanate (780 mg) and toluene (10 ml) was stirred at 70–80° C. for 20 hrs. The reaction mixture was concentrated. The residue was purified by silica gel column chromatography and 3-(4-(4-chlorophenyl)-2-([(tert-butylamino)carbonyl]amino}-5-thiazolyl)-N-[4-(diethylphosphonomethyl)phenyl]propionamide was obtained as crystals (395 mg, yield: 83%) from a fraction eluted with 3% methanol-ethyl acetate. Recrystallization from ethyl acetate gave colorless prism crystals. melting point: 180–181° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b04843e63a2d4a3aae5931f8f12eb41a
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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