Sodium Hydroxide → HCID 68751793, compound

HRID 1614868Notes

Reaction equation

HRID 1614868 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C@H:11]2[CH2:15][CH2:14][C@@H:13]([C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=3)[CH2:12]2)[CH3:9])=[CH:4][C:3]=1[O:26][CH3:27].[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C@H:11]2[CH2:15][CH2:14][C@@H:13]([C:16]3[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:24][CH:25]=3)[CH2:12]2)[CH3:9])=[CH:4][C:3]=1[O:26][CH3:27]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68749897HCID 68749897, compound

Product 1

HCID 68751793HCID 68751793, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-[(1R,3S)-3-[[(1R)-1-(4-fluoro-3-methoxyphenyl)ethyl]amino]-cyclopentyl]benzoate (preparation 33) (89 mg) in methanol (1 mL) was treated with 2M NaOH at r.t. for 2 h. After removal of the solvent in vacuo, 2M acetic acid was added to pH 4. The resulting precipitate was collected on a filter, washed with water and dried to afford the title compound. 1H NMR (300 MHz, DMSO) δ 7.78 (d, J=8.1 Hz, 2H), 7.18 (d, J=8.2 Hz, 3H), 7.10 (dd, J=11.5, 8.3 Hz, 1H), 6.89 (ddd, J=8.2, 4.5, 1.9 Hz, 1H), 3.85-3.73 (m, 4H), 2.98-2.82 (m, 2H), 2.14-2.01 (m, 1H), 1.97-1.54 (m, 4H), 1.36 (td, J=11.7, 8.9 Hz, 1H), 1.25 (d, J=6.6 Hz, 3H).

Workup

  1. customAfter removal of the solvent in vacuo, 2M acetic acid
  2. additionwas added to pH 4
  3. customThe resulting precipitate was collected on a filter
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-87833ebc6a2e4fa98fe5606760cf32cb
Source dataset
uspto-grants-2014_07
Patent number
US08765676B2

Reaction notes

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