Hydrochloric Acid → HCID 69817718, compound

HRID 2417439Notes

Reaction equation

HRID 2417439 reaction equation
[CH2:1]([N:8]([C@H:20]([CH2:41][OH:42])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([C:31]2[CH:40]=[CH:39][C:34]([C:35]([O:37]C)=[O:36])=[CH:33][CH:32]=2)=[O:30])=[CH:24][CH:23]=1)[CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[CH2:1]([N:8]([C@H:20]([CH2:41][OH:42])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([C:31]2[CH:40]=[CH:39][C:34]([C:35]([OH:37])=[O:36])=[CH:33][CH:32]=2)=[O:30])=[CH:24][CH:23]=1)[CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69817809HCID 69817809, compound

Product 1

HCID 69817718HCID 69817718, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-[[[4-[(2S)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-3-hydroxypropyl]-phenyl]amino]carbonyl]benzoate (93.6 mg) in methanol (2.0 ml) was added 1N sodium hydroxide solution (329 μl) and the solution was refluxed for 2.5 hours. After cooling to room temperature, the mixture was neutralized by the addition of 1N hydrochloric acid (329 μl). The solvent was removed by evaporation and the residual solid was suspended in water (2.0 ml). The solid was collected by filtration, washed with water, and dried under reduced pressure to give 4-[[[4-[(2S)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-3-hydroxypropyl]phenyl]amino]carbonyl]benzoic acid (80.2 mg) as a white solid.

Workup

  1. temperaturethe solution was refluxed for 2.5 hours
  2. customThe solvent was removed by evaporation
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-7ab81db95abb4d7c87431cbb1fcee1bf
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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