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Benzenemethanesulfonamide → Benzamide, 3-(((1S)-2-(4,5-diphenyl-2-oxazolyl)-2-cyclohexen-1-yl)methyl)-N-((phenylmethyl)sulfonyl)-

HRID 2305227
Notes
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Reaction equation

HRID 2305227 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](O)=[O:29])[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.[C:34]1([CH2:40][S:41]([NH2:44])(=[O:43])=[O:42])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.CN(C)C1C=CN=CC=1.CCOC(C)=O>[CH2:40]([S:41]([NH:44][C:28](=[O:29])[C:27]1[CH:31]=[CH:32][CH:33]=[C:25]([CH2:24][C@@H:19]2[CH2:20][CH2:21][CH2:22][CH:23]=[C:18]2[C:9]2[O:10][C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)[CH:26]=1)(=[O:42])=[O:43])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 78318BenzenemethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9955802HCID 9955802, compound

Product 1

HCID 9894720Benzamide, 3-(((1S)-2-(4,5-diphenyl-2-oxazolyl)-2-cyclohexen-1-yl)methyl)-N-((phenylmethyl)sulfonyl)-Yield 64%

Reagents, catalysts & solvents 3

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 3-{[(1S)-2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzoic acid (250 mg, 0.575 mmol) and α-toluenesulfonamide (98 mg, 0.575 mmol) in DMF (6 ml) was added 4-dimethylaminopyridine (105 mg, 0.863 mmol) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (220 mg, 1.15 mmol). After stirring the resulting mixture at room temperature for 16 hours, the reaction mixture was diluted with EtOAc (30 ml), washed with 1N-hydrochloric acid, water and brine successively, dried over dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:EtOAc, 1:1 elution) to give N-benzylsulfonyl-3-{[(1S)-2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzamide (216.4 mg, 64%).

Workup

  1. washwashed with 1N-hydrochloric acid, water and brine successively
  2. customdried
  3. dry with materialover dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (hexane:EtOAc, 1:1 elution)

Sources & evidence

ORD record
ord-41f18cac56eb4ab0b0f5d8bfcff86adf
Source dataset
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06437146B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes