Sodium Hydroxide → HCID 58641185, compound

HRID 1394958Notes

Reaction equation

HRID 1394958 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([CH2:14][CH2:15][C:16]([O:18]C)=[O:17])[C@H:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:10]=1.[OH-].[Na+]>CC(O)(C)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C@H:11]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58641266HCID 58641266, compound

Product 1

HCID 58641185HCID 58641185, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of methyl 3-[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]propanoate (37-8, 200 mg, 0.582 mmol, 1 equiv) and sodium hydroxide (1N, 1.16 mL, 1.16 mmol, 2.00 equiv) in t-BuOH (5 mL) was heated at 50° C. for 2 h. The reaction mixture was concentrated and the residue was partitioned between brine made acidic with aqueous 1 N HCL solution (1.2 mL) and ethyl acetate (2×40 mL). The combined organic layers were dried over sodium sulfate and concentrated to give 3-[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]propanoic acid (39-1) as a white foam. LRMS m/z (M+H) 330.1 found, 330.3 required.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between brine
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-caa4893a3515425d91effbf9cdf6b72e
Source dataset
uspto-grants-2008_03
Patent number
US07348440B2

Reaction notes

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