Sodium Hydroxide → (S)-2-(4-{2-[5-Methyl-2-(5-methyl-thiophen-2-yl)-oxazol-4-yl]-ethoxy}-benzyl)-2-phenoxy-butyric Acid

HRID 585267Notes

Reaction equation

HRID 585267 reaction equation
C([O:3][C:4](=[O:37])[C@:5]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][C:25]2[N:26]=[C:27]([C:31]3[S:32][C:33]([CH3:36])=[CH:34][CH:35]=3)[O:28][C:29]=2[CH3:30])=[CH:18][CH:17]=1)([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:6][CH3:7])C.[OH-].[Na+]>CO>[CH3:30][C:29]1[O:28][C:27]([C:31]2[S:32][C:33]([CH3:36])=[CH:34][CH:35]=2)=[N:26][C:25]=1[CH2:24][CH2:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][C@@:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([CH2:6][CH3:7])[C:4]([OH:37])=[O:3])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69316116(S)-2-(4-{2-[5-Methyl-2-(5-methyl-thiophen-2-yl)-oxazol-4-yl]-ethoxy}-benzyl)-2-phenoxy-butyric Acid Ethyl Ester

Product 1

HCID 69316491(S)-2-(4-{2-[5-Methyl-2-(5-methyl-thiophen-2-yl)-oxazol-4-yl]-ethoxy}-benzyl)-2-phenoxy-butyric Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

(S)-2-(4-{2-[5-Methyl-2-(5-methyl-thiophen-2-yl)-oxazol-4-yl]-ethoxy}-benzyl)-2-phenoxy-butyric acid ethyl ester (201 mg, 0.40 mmol) in MeOH (8 mL) was treated with 2N NaOH (8 mL) and warmed to 55° C. After 18 h, the mixture was concentrated under reduced pressure and then acidified with 5N HCl to pH=1. The solution was extracted with EtOAc and then the organic phases dried (MgSO4), filtered and concentrated to a white foam (158 mg, 81%) that was dried in a vacuum oven at 50° C. for 24 h: 1H NMR (400 MHz, CDCl3) δ 7.36 (d, J=3.6 Hz, 1H), 7.16 (t, J=8.0 Hz, 2H), 7.10 (d, J=8.4 Hz, 2H), 6.96 (t, J=7.2 Hz, 1H), 6.83 (d, J=7.6 Hz, 2H), 6.75 (d, J=8.8 Hz, 2H), 6.71 (dd, J=3.6, 0.8 Hz, 1H), 4.13 (t, J=6.8 Hz, 2H), 3.18 (A of Abq, J=13.6 Hz, 1H), 3.00 (B of Abq, J=13.6 Hz, 1H), 2.90 (t, J=6.8 Hz, 2H), 2.49 (s, 3H), 2.31 (s, 3H), 1.31 (s, 3H).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. extractionThe solution was extracted with EtOAc
  3. dry with materialthe organic phases dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to a white foam (158 mg, 81%) that
  6. customwas dried in a vacuum oven at 50° C. for 24 h

Sources & evidence

ORD record
ord-719bf570dd354e9abcfe1530aa189ffd
Source dataset
uspto-grants-2005_08
Patent number
US06930120B2

Reaction notes

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