Sodium Hydroxide → HCID 60024293, compound

HRID 1393471Notes

Reaction equation

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

Participants

Conditions

Temperature: 55 °C

Procedure

(S)-2-Methyl-3-{4-[2-(5-methyl-2-phenethyl-oxazol-4-yl)-ethoxy]-phenyl}-2-phenoxy-propionic acid ethyl ester (340 mg, 0.66 mmol) in MeOH (10 mL) was treated with 2N NaOH (10 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 (273 mg, 85%): 1H NMR (400 MHz, CDCl3) δ 9.00 (br s, 1H), 7.27-7.15 (m, 9H), 6.95 (t, J=7.3 Hz, 1H), 6.91 (d, J=7.7 Hz, 2H), 6.78 (d, J=7.7 Hz, 2H), 4.10 (t, J=6.2 Hz, 2H), 3.27 (A of ABq, J=13.9 Hz, 1H), 3.13 (B of ABq, J=13.9 Hz, 1H), 3.04 (s, 4H), 2.89 (t, J=6.2 Hz, 2H), 2.26 (s, 3H), 1.41 (s, 3H); MS (EI+) 486.1 (M+H), (EI−) 484.1 (M−H).

Workup

concentrationthe mixture was concentrated under reduced pressure
extractionThe solution was extracted with EtOAc
dry with materialthe organic phases dried (MgSO4)
filtrationfiltered
concentrationconcentrated to a white foam (273 mg, 85%)

Sources & evidence

ORD record: ord-9b37db4245844468823aea0e363bcf7b
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07345070B2

Reaction notes

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