Benzenesulfonic Acid → 4-({[({[(2S)-4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}amino)carbonyl]amino}methyl)benzamide benzenesulfonate dihydrate

HRID 492116Notes

Reaction equation

HRID 492116 reaction equation
[C:1]1([S:7]([OH:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[Cl:12][C:13]1[CH:14]=[C:15]([CH:38]=[CH:39][C:40]=1[Cl:41])[CH2:16][N:17]1[CH2:22][CH2:21][O:20][C@@H:19]([CH2:23][NH:24][C:25]([NH:27][CH2:28][C:29]2[CH:37]=[CH:36][C:32]([C:33]([NH2:35])=[O:34])=[CH:31][CH:30]=2)=[O:26])[CH2:18]1>C(O)(C)C>[OH2:8].[OH2:20].[C:1]1([S:7]([OH:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:38]=[CH:39][C:40]=1[Cl:41])[CH2:16][N:17]1[CH2:22][CH2:21][O:20][C@@H:19]([CH2:23][NH:24][C:25]([NH:27][CH2:28][C:29]2[CH:37]=[CH:36][C:32]([C:33]([NH2:35])=[O:34])=[CH:31][CH:30]=2)=[O:26])[CH2:18]1

Participants

4

Reactant 2

HCID 7371Benzenesulfonic AcidHCID 690695974-({[({[(2S)-4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}amino)carbonyl]amino}methyl) benzamide hydrate

Product 1

HCID 866046714-({[({[(2S)-4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}amino)carbonyl]amino}methyl)benzamide benzenesulfonate dihydrate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The slurry of Description 9 was cooled to 50±3° and isopropanol (30 ml) added, followed by an aqueous solution of benzene sulfonic acid (32% w/v, 10 ml). The mixture was cooled to 22±3° over ca 1 h, seeded with authentic 4-({[({[(2S)-4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}amino)carbonyl]amino}methyl) benzamide hydrate and aged at 22±3° for 72 h. The mixture was cooled to 0±3° over 1 h and filtered. The filter cake was washed with a 4:1:0.1 mixture of isopropyl acetate/isopropyl alcohol/water (2.5 ml) and dried in vacuo at 25±5° to give the title compound as a white solid (6.9 g).

Workup

  1. temperatureThe slurry of Description 9 was cooled to 50±3°
  2. temperatureThe mixture was cooled to 22±3° over ca 1 h
  3. temperatureThe mixture was cooled to 0±3° over 1 h
  4. filtrationfiltered
  5. washThe filter cake was washed with a 4:1:0.1 mixture of isopropyl acetate/isopropyl alcohol/water (2.5 ml)
  6. customdried in vacuo at 25±5°

Sources & evidence

ORD record
ord-bc381bbcb1f2457d8c416961da710763
Source dataset
uspto-grants-2009_05
Patent number
US07531651B2

Reaction notes

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