Ammonia → HCID 54444195, compound

HRID 1067127Notes

Reaction equation

HRID 1067127 reaction equation
[C:1]1([C:7]2N=[C:9]([C:18]3[CH:23]4[CH2:24][CH:20]([CH2:21][CH2:22]4)[C:19]=3[CH2:25][C:26]3[CH:27]=C([CH:32]=[CH:33][CH:34]=3)C(O)=O)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C[O:38]CC1.ClC(OCC(C)C)=O.[NH3:48].C([N:51]([CH2:54][CH3:55])CC)C>>[C:1]1([C:7]2[N:48]=[C:9]([C:18]3[CH:23]4[CH2:24][CH:20]([CH2:21][CH2:22]4)[C:19]=3[CH2:25][C:26]3[CH:27]=[C:55]([CH:32]=[CH:33][CH:34]=3)[C:54]([NH2:51])=[O:38])[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 5

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 54433463HCID 54433463, compound

Product 1

HCID 54444195HCID 54444195, compound

Procedure

To a solution of 3-{[3-(4,5-diphenyloxazol-2-yl)-bicyclo[2.2.1]hept-2-en-2-yl]methyl}benzoic acid (0.46 g) in a THF (10 ml) were added isobutyl chloroformate (0.26 ml) and triethylamine (0.3 ml) at 0° C. under N2. After being stirred for 30 minutes, NH3 (5 ml, 4M solution in methanol) was added to the mixture. After being stirred for 30 minutes, the solvent was removed in vacuo. The residue was partitioned between ethyl acetate and lN-NaOH and the organic layer was washed with brine. The dried solvent was evaporated in vacuo to give 3-{[3-(4,5-diphenyloxazol-2-yl)bicyclo[2.2.1]hept-2-en-2-yl]methyl}benzamide (0.2 g).

Workup

  1. stirringAfter being stirred for 30 minutes
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between ethyl acetate
  4. washthe organic layer was washed with brine
  5. customThe dried solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-d8e401a1ccc34cee85508e9956821e45
Source dataset
uspto-grants-2001_06
Patent number
US06245790B1

Reaction notes

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