p-Toluenesulfonic acid → HCID 178448170, compound

HRID 274769Notes

Reaction equation

HRID 274769 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-64497c8df9ad46f981c861180039dbfa
Source dataset
uspto-grants-1995_02
Patent number
US05389616

Reaction notes

Loading…