1,4-Dioxane hydrochloride → HCID 86628555, compound

HRID 732690Notes

Reaction equation

HRID 732690 reaction equation
C[S:2]([NH:5][C:6]([C:8]1[CH:47]=[CH:46][C:11]([C:12]([N:14]2[CH2:18][C@H:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C@@H:16]([CH2:25][N:26]([C@@H:34]([C:36]3C4C(=CC=CC=4)[CH:39]=[CH:38][CH:37]=3)[CH3:35])C(=O)OC(C)(C)C)[CH2:15]2)=[O:13])=[CH:10][CH:9]=1)=[O:7])(=[O:4])=[O:3].Cl.[O:49]1[CH2:54]COCC1>O1CCOCC1>[CH3:54][O:49][S:2]([NH:5][C:6](=[O:7])[C:8]1[CH:47]=[CH:46][C:11]([C:12]([N:14]2[CH2:18][C@H:17]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C@@H:16]([CH2:25][NH:26][C@@H:34]([C:36]3[C:47]4[C:8](=[CH:9][CH:10]=[CH:11][CH:46]=4)[CH:39]=[CH:38][CH:37]=3)[CH3:35])[CH2:15]2)=[O:13])=[CH:10][CH:9]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86628556HCID 86628556, compound

Product 1

HCID 86628555HCID 86628555, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 1.6 ml 1,4-dioxane solution of 160 mg of tert-butyl {[(3R,4S)-1-(4-{[(methylsulfonyl)amino]carbonyl}benzoyl)-4-phenylpyrrolidin-3-yl]methyl}[(1R)-1-(1-naphthyl)ethyl]carbamate was mixed with 1.5 ml of 4 M hydrogen chloride/1,4-dioxane and stirred at room temperature for 4Hours. The reaction solution was concentrated under a reduced pressure and dissolved in water. This was neutralized with saturated sodium bicarbonate solution and extracted with chloroform. The organic layer was dried with anhydrous sodium sulfate and then concentrated under a reduced pressure. The thus obtained residue was crystallized with ethyl acetate to obtain 85 mg of N-(methoxysulfonyl)-4-{[(3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}benzamide as colorless crystals.

Workup

  1. concentrationThe reaction solution was concentrated under a reduced pressure
  2. dissolutiondissolved in water
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customThe thus obtained residue was crystallized with ethyl acetate

Sources & evidence

ORD record
ord-b0fb6834c0124406ba580cf33d73cf4e
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

Loading…