Sodium Hydroxide → 4-biphenyl-4-ylmethyl-1-[2-(S)-tert-butoxycarbonylamino-3-thiophen-2-yl-propionyl]-piperidine-4-carboxylic acid

HRID 2360968Notes

Reaction equation

HRID 2360968 reaction equation
C[O:2][C:3]([C:5]1([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:31][CH:30]=2)[CH2:10][CH2:9][N:8]([C:11](=[O:27])[C@@H:12]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+]>C1COCC1.CO>[C:32]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:33]=[CH:34][C:29]([CH2:28][C:5]2([C:3]([OH:4])=[O:2])[CH2:10][CH2:9][N:8]([C:11](=[O:27])[C@@H:12]([NH:19][C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH2:13][C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)[CH2:7][CH2:6]2)=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 673851184-biphenyl-4-ylmethyl-1-[2-(S)-tert-butoxycarbonylamino-3-thiophen-2-yl-propionyl]-piperidine-4-carboxylic acid methyl ester

Product 1

HCID 673846684-biphenyl-4-ylmethyl-1-[2-(S)-tert-butoxycarbonylamino-3-thiophen-2-yl-propionyl]-piperidine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-biphenyl-4-ylmethyl-1-[2-(S)-tert-butoxycarbonylamino-3-thiophen-2-yl-propionyl]-piperidine-4-carboxylic acid methyl ester (5.63 mmol; 3.17 g) in THF (30 mL) and methanol (20 mL) was added a 1M solution of sodium hydroxide (16.9 mmol; 16.9 mL) and the resulting mixture was heated to reflux for 48 hours. The resulting mixture was then evaporated and a 1N hydrochloric acid solution (200 mL) was added to the residue. A white precipitate formed that was separated via filtration to yield 4-biphenyl-4-ylmethyl-1-[2-(S)-tert-butoxycarbonylamino-3-thiophen-2-yl-propionyl]-piperidine-4-carboxylic acid. MS (ESI) m/z 547.44 [M+H]+.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 48 hours
  3. customThe resulting mixture was then evaporated
  4. additiona 1N hydrochloric acid solution (200 mL) was added to the residue
  5. customA white precipitate formed
  6. customthat was separated via filtration

Sources & evidence

ORD record
ord-bd0a050957354836b87182b3ab7d7894
Source dataset
uspto-grants-2014_04
Patent number
US08686152B2

Reaction notes

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