Hydrochloric Acid → 2-amino-4-[(1R)-1-({[(6R)-6-(5-chloro-2-methoxybenzyl)-7-oxo-3-(phenoxyimino)-1,4-diazepan-1-yl]carbonyl}amino)propyl]benzoic acid hydrochloride

HRID 80587Notes

Reaction equation

HRID 80587 reaction equation
[NH2:1][C:2]1[CH:14]=[C:13]([C@H:15]([NH:18][C:19]([N:21]2[C:27](=[O:28])[C@H:26]([CH2:29][C:30]3[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=3[O:37][CH3:38])[CH2:25][NH:24][C:23](=[N:39][O:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:22]2)=[O:20])[CH2:16][CH3:17])[CH:12]=[CH:11][C:3]=1[C:4]([O:6]C(C)(C)C)=[O:5].Cl>C(O)(=O)C>[ClH:36].[NH2:1][C:2]1[CH:14]=[C:13]([C@H:15]([NH:18][C:19]([N:21]2[C:27](=[O:28])[C@H:26]([CH2:29][C:30]3[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=3[O:37][CH3:38])[CH2:25][NH:24][C:23](=[N:39][O:40][C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH2:22]2)=[O:20])[CH2:16][CH3:17])[CH:12]=[CH:11][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178456086HCID 178456086, compound

Product 1

HCID 1784560872-amino-4-[(1R)-1-({[(6R)-6-(5-chloro-2-methoxybenzyl)-7-oxo-3-(phenoxyimino)-1,4-diazepan-1-yl]carbonyl}amino)propyl]benzoic acid hydrochlorideYield 161.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To the compound 77a (523 mg) obtained at Step (1), 1M hydrochloric acid in acetic acid solution (18 ml) was added, and the mixture was stirred at room temperature for 2.5 hours. The reaction solution was concentrated, then the residue was diluted with ethyl acetate. To this solution, a 1M hydrochloric acid in acetic acid solution was added and the mixture was stirred. Further, diethyl ether was added, and the precipitated solid was collected by filtration to obtain the title compound (410 mg).

Workup

  1. additionwas added
  2. concentrationThe reaction solution was concentrated
  3. additionthe residue was diluted with ethyl acetate
  4. additionTo this solution, a 1M hydrochloric acid in acetic acid solution was added
  5. stirringthe mixture was stirred
  6. additionFurther, diethyl ether was added
  7. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-149984a2e97141098b22c88ceba91bee
Source dataset
uspto-grants-2014_09
Patent number
US08846660B2

Reaction notes

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