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Ammonia → HCID 54201772, compound

HRID 1067120
Notes
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Reaction equation

HRID 1067120 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]([C:18]3[C@H:19]([CH2:24][C:25]4[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=4)[C:28]([NH2:47])=[O:30])[CH2:20][CH2:21][CH2:22][CH:23]=3)[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

HCID 54201772HCID 54201772, 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 (0.3 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 lN-NaOH and the organic layer was washed with brine. The dried solvent 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 (S)-3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}- benzamide (0.03 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
  6. customThe residue was purified by chromatography on silica gel
  7. customto give
  8. customthe obtained residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f4e6239afd0e4dd7a4b3021620b9d68a
Source dataset
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06245790B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes