1,4-Dioxane hydrochloride → HCID 68914533, compound

HRID 732686Notes

Reaction equation

HRID 732686 reaction equation
[NH2:1][S:2]([C:5]1[CH:44]=[CH:43][C:8]([C:9]([N:11]2[CH2:15][C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@@H:13]([CH2:22][N:23]([C@@H:31]([C:33]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH:36]=[CH:35][CH:34]=3)[CH3:32])C(=O)OC(C)(C)C)[CH2:12]2)=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl.O1CCOCC1>O1CCOCC1>[C:33]1([C@H:31]([NH:23][CH2:22][C@@H:13]2[C@@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:15][N:11]([C:9]([C:8]3[CH:43]=[CH:44][C:5]([S:2]([NH2:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)=[O:10])[CH2:12]2)[CH3:32])[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86628551HCID 86628551, compound

Product 1

HCID 68914533HCID 68914533, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 1.6 ml 1,4-dioxane solution of 110 mg of tert-butyl ({(3R,4S)-1-[4-(aminosulfonyl)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 60Hours. The reaction solution was concentrated under a reduced pressure, mixed with water and neutralized with saturated sodium bicarbonate solution. The organic layer extracted with chloroform was dried with anhydrous sodium sulfate and then concentrated under a reduced pressure. By crystallizing the thus obtained residue from ethyl acetate, 65 mg of 4-{[(3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}benzene sulfonamide was obtained as colorless crystals.

Workup

  1. concentrationThe reaction solution was concentrated under a reduced pressure
  2. additionmixed with water and neutralized with saturated sodium bicarbonate solution
  3. extractionThe organic layer extracted with chloroform
  4. dry with materialwas dried with anhydrous sodium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customBy crystallizing the thus obtained residue from ethyl acetate

Sources & evidence

ORD record
ord-6d2b8a2b3ff648d3a987b0d236b47c11
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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