Ammonia → HCID 9888387, compound

HRID 1067123Notes

Reaction equation

HRID 1067123 reaction equation
O1CCCC1.[C:6]1([C:12]2[N:13]=[C:14]([C:23]3[CH:24]([CH2:28][C:29]4[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=4)[C:32]([OH:34])=O)[CH2:25][CH2:26][CH:27]=3)[O:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.ClC(OCC)=O.[NH3:44]>C(N(CC)CC)C>[C:6]1([C:12]2[N:13]=[C:14]([C:23]3[CH:24]([CH2:28][C:29]4[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=4)[C:32]([NH2:44])=[O:34])[CH2:25][CH2:26][CH:27]=3)[O:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 9802285HCID 9802285, compound

Product 1

HCID 9888387HCID 9888387, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a tetrahydrofuran solution (10 ml) of 3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclopenten-1-yl]methyl}benzoic acid (0.30 g) and triethylamine (0.15 ml) was added ethyl chloroformate (0.15 ml) at 0° C. The solution was stirred for 30 minutes at the same temperature. Then aqueous ammonia (10 ml) was added to the solution. After stirred for 6 hours at 0° C., the solution was partitioned between ethyl acetate and water. The organic layer was washed with water, 1N hydrochloric acid, water and brine. After dried over MgSO4, the solvent was evaporated in vacuo to afford 3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclopenten-1-yl]methyl}benzamide (0.24 g).

Workup

  1. stirringAfter stirred for 6 hours at 0° C.
  2. customthe solution was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water, 1N hydrochloric acid, water and brine
  4. dry with materialAfter dried over MgSO4
  5. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-68aa1ef34a07448286cf7e0afcded677
Source dataset
uspto-grants-2001_06
Patent number
US06245790B1

Reaction notes

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