Hydrochloric Acid → HCID 18739118, compound

HRID 1934690Notes

Reaction equation

HRID 1934690 reaction equation
C(OC([N:8]1[C@H:12]([CH2:13][OH:14])[CH2:11][C@H:10]([NH:15][C:16]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][C:17]=2[C:18]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=2)=[O:19])[CH2:9]1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[O:30]([C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][C:25]=1[O:28][CH3:29])[CH2:21][NH:20][C:18](=[O:19])[C:17]1[CH:32]=[C:33]([N+:36]([O-:38])=[O:37])[CH:34]=[CH:35][C:16]=1[NH:15][C@H:10]1[CH2:11][C@@H:12]([CH2:13][OH:14])[NH:8][CH2:9]1)[CH3:31]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18739113HCID 18739113, compound

Product 1

HCID 18739118HCID 18739118, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-[(3S,5S)-1-(tert-butoxycarbonyl)-5-(hydroxymethyl)pyrrolidin-3-ylamino]-N-(3,4-dimethoxylbenzyl)-5-nitrobenzamide (326 mg) and 4N-hydrogen chloride solution in ethyl acetate (5 mL) was stirred for one day at ambient temperature. After evaporation of the solvent, the residue was partitioned between chloroform and an aqueous saturated sodium bicarbonate solution. The organic layer was separated, washed with brine and dried over magnesium sulfate. The filtrate was evaporated to give N-(3,4-dimethoxylbenzyl)-2-[(3S,5S)-5-(hydroxymethyl)pyrrolidin-3-ylamino]-5-nitrobenzamide (242 mg) as pale yellow foams.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was partitioned between chloroform
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-08d71e995d8b4c2da41869a286427f64
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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