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

HRID 492115Notes

Reaction equation

HRID 492115 reaction equation
ClC1C=C(C=CC=1Cl)CN1CC[O:9][C@@H](CNC(NCC2C=CC(C(N)=O)=CC=2)=O)C1.C1(S(O)(=O)=[O:38])C=CC=CC=1.C(OC(C)C)(=O)C.O.[C:49]1([S:55]([OH:58])(=[O:57])=[O:56])[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1.[Cl:59][C:60]1[CH:61]=[C:62]([CH:85]=[CH:86][C:87]=1[Cl:88])[CH2:63][N:64]1[CH2:69][CH2:68][O:67][C@@H:66]([CH2:70][NH:71][C:72]([NH:74][CH2:75][C:76]2[CH:84]=[CH:83][C:79]([C:80]([NH2:82])=[O:81])=[CH:78][CH:77]=2)=[O:73])[CH2:65]1>C(O)C.O.C1CCCCC1>[OH2:9].[OH2:38].[C:49]1([S:55]([OH:58])(=[O:57])=[O:56])[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1.[Cl:59][C:60]1[CH:61]=[C:62]([CH:85]=[CH:86][C:87]=1[Cl:88])[CH2:63][N:64]1[CH2:69][CH2:68][O:67][C@@H:66]([CH2:70][NH:71][C:72]([NH:74][CH2:75][C:76]2[CH:84]=[CH:83][C:79]([C:80]([NH2:82])=[O:81])=[CH:78][CH:77]=2)=[O:73])[CH2:65]1

Participants

8

Reactant 4

HCID 7371Benzenesulfonic AcidHCID 7915Isopropyl AcetateHCID 10218765GW-766994HCID 866046724-({[({[(2S)-4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}amino)carbonyl]amino}methyl) benzamide benzenesulfonate hydrate

Product 1

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

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolvent3×HCID 8078CyclohexaneSolvent2×

Conditions

Temperature
0 °C

Procedure

4-({[({[(2S)-4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}amino)carbonyl]amino}-methyl)benzamide (15 g) was suspended in ethanol (60 ml) and water (7.5 ml) at 40° C. A solution of benzene sulfonic acid (6.0 g) in water (7.5 ml) was added, followed by addition of further water (15 ml). Isopropyl acetate (300 ml) was added at 40° C., followed by addition of ethanol (40 ml). The mixture was cooled to 0° C., diluted with cyclohexane (10 ml) and seeded with authentic 4-({[({[(2S)-4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}amino)carbonyl]amino}methyl) benzamide benzenesulfonate hydrate. The mixture was chilled at 0° C. over 1 h, cyclohexane (100 ml) added over 15 min and the mixture aged at 0° C. The product was isolated by vacuum filtration, washed with isopropyl acetate (2×30 ml) and dried in vacuo at 25±5° to give the title compound as a white solid (16.44 g).

Workup

  1. customat 40° C
  2. temperatureThe mixture was chilled at 0° C. over 1 h
  3. customaged at 0° C
  4. customThe product was isolated by vacuum filtration
  5. washwashed with isopropyl acetate (2×30 ml)
  6. customdried in vacuo at 25±5°

Sources & evidence

ORD record
ord-8ed2431020ed45c8b6f7708578c7a1e2
Source dataset
uspto-grants-2009_05
Patent number
US07531651B2

Reaction notes

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