Ammonia → HCID 56988666, compound

HRID 1067121Notes

Reaction equation

HRID 1067121 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[C@H:19]([CH2:24][C:25]4[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=4)[C:28]([OH:30])=O)[CH2:20][CH2:21][CH2:22][CH:23]=3)[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.O1CCCC1.ClC(OCC(C)C)=O.[NH3:47]>C(N(CC)CC)C>[C:1]1([C:7]2[N:8]=[C:9]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]3[CH2:24][C:25]3[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=3)[C:28]([NH2:47])=[O:30])[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 62365Isobutyl chloroformateHCID 9955802HCID 9955802, compound

Product 1

HCID 56988666HCID 56988666, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of (S)-3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzoic acid (0.2 g) in a tetrahydrofuran (10 ml) were added isobutyl chloroformate (0.15 ml.) and triethylamine (0.2 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 1N-NaOH and the organic layer was washed with brine. The dried solvent was evaporated in vacuo. The residue and 10% Pd/C (0.2 g) in methanol (20 ml) was stirred under H2 for 8 hours. The catalyst was filtered off and filtrate was evaporated in vacuo. The residue was purified by chromatography on silica gel to give and the obtained residue was purified by chromatography on silica gel to give 3-{[(1S)-2-(4,5-diphenyloxazol-2-yl)-1-cyclohexyl]methyl}benzamide (0.11 g).

Workup

  1. stirringAfter being stirred for 30 minutes
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between ethyl acetate and 1N-NaOH
  4. washthe organic layer was washed with brine
  5. customThe dried solvent was evaporated in vacuo
  6. stirringThe residue and 10% Pd/C (0.2 g) in methanol (20 ml) was stirred under H2 for 8 hours
  7. filtrationThe catalyst was filtered off
  8. customfiltrate was evaporated in vacuo
  9. customThe residue was purified by chromatography on silica gel
  10. customto give
  11. customthe obtained residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e25eaf609c824e819e8567c22db4b41b
Source dataset
uspto-grants-2001_06
Patent number
US06245790B1

Reaction notes

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