Sodium Hydroxide → HCID 20672369, compound

HRID 1386707Notes

Reaction equation

HRID 1386707 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH2:20][C@@H:21]3[C@@H:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:24][N:23]([C@H:32]([CH:36]4[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]4)[C:33]([OH:35])=[O:34])[CH2:22]3)[CH2:16][CH2:15]2)=[CH:7][CH:6]=1)([O:3]C)=[O:2].[OH-].[Na+]>CO>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([CH2:20][C@@H:21]3[C@@H:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:24][N:23]([C@H:32]([CH:36]4[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]4)[C:33]([OH:35])=[O:34])[CH2:22]3)[CH2:18][CH2:19]2)=[CH:7][CH:6]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20672368HCID 20672368, compound

Product 1

HCID 20672369HCID 20672369, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 27 mg (0.05 mmol) of 2-(R)-(3-(S)-(4-(3-(4-(carbomethoxy)phenyl)propyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-3-methylbutanoic acid (from EXAMPLE 29, Step D) in 3 mL of MeOH was treated with 0.2 mL of 5.0 N NaOH and the resulting mixture was heated at reflux for 1 h. The mixture was cooled and concentrated. The residue was partially dissolved in H2O and the solids filtered and dried to afford 11 mg (42%, 2 steps) of the title compound: ESI-MS 547 (M+H); HPLC B: 6.57 min.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 1 h
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. dissolutionThe residue was partially dissolved in H2O
  6. filtrationthe solids filtered
  7. customdried

Sources & evidence

ORD record
ord-8875ae9a6c434e2fb0880abe6126d321
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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