p-Toluenesulfonic acid → HCID 178448170, compound

HRID 1657254Notes

Reaction equation

HRID 1657254 reaction equation
[C:1]([S:5]([CH2:8][C@@H:9]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:10]([NH:12][C@@H:13]([CH2:32][C:33]1[N:34]=[CH:35][NH:36][CH:37]=1)[C:14]([NH:16][C@@H:17]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C@@H:18]([OH:24])[C@@H:19]([OH:23])[CH:20]([CH3:22])[CH3:21])=[O:15])=[O:11])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].[C:45]1(C)[CH:50]=CC(S(O)(=O)=O)=C[CH:46]=1.C(=O)(O)[O-].[Na+]>COC(OC)(C)C>[C:1]([S:5]([CH2:8][C@@H:9]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:10]([NH:12][C@@H:13]([CH2:32][C:33]1[N:34]=[CH:35][NH:36][CH:37]=1)[C:14]([NH:16][C@@H:17]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C@@H:18]1[C@H:19]([CH:20]([CH3:21])[CH3:22])[O:23][C:45]([CH3:50])([CH3:46])[O:24]1)=[O:15])=[O:11])(=[O:7])=[O:6])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 178448391HCID 178448391, compound

Product 1

HCID 178448170HCID 178448170, compound

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

50 mg of (S)-α-[(S)-α-[(t-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-2,3-dihydroxy-4-methylpentyl]imidazole-4-propionamide and 50 mg of p-toluenesulphonic acid in 3 ml of dimethoxypropane are stirred at room temperature overnight. The reaction mixture is thereafter poured into 2N sodium bicarbonate solution and extracted with ethyl acetate. The organic phases are washed with water, dried and evaporated, whereby there is obtained (S)-α-[(S)-α-[(t-butylsulphonyl)methyl]hydrocinnamamido]-N-[(S)-(cyclohexylmethyl)[(4R,5S)-5-isopropyl-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]imidazole-4-propionamide as a solid, MS: 673 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phases are washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-c241f304d6524779888cb370301c9e46
Source dataset
uspto-grants-1993_10
Patent number
US05256645

Reaction notes

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