Hydrochloric Acid → HCID 18510724, compound

HRID 1370260Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

) A mixture of compound (56) (0.001 mol) in methanol (100 ml) was cooled to 0° C. NaOH 1N (0.0288 mol) was added and the reaction mixture was stirred overnight at RT. The reaction mixture was re-cooled to 0° C. 1 N HCl (30 ml) was added and this mixture was extracted with CH2Cl2. The separated organic layer was dried (MgSO4), filtered and the solvent evaporated under reduced pressure. The residue was crystallized from ethanol. The precipitate was filtered off, washed with ethanol, and dried, yielding 0.2 g (5.2%) (±)-4-[[[4,5-dihydro-3-(3-pyridinyl)-5-isoxazolyl]carbonyl]amino]-α-phenylbenzeneacetic acid (compound 406).

Workup

temperatureThe reaction mixture was re-cooled to 0° C
extractionthis mixture was extracted with CH2Cl2
dry with materialThe separated organic layer was dried (MgSO4)
filtrationfiltered
customthe solvent evaporated under reduced pressure
customThe residue was crystallized from ethanol
filtrationThe precipitate was filtered off
washwashed with ethanol
customdried

Sources & evidence

ORD record: ord-dbc765cf892e440299211140b731ccdc
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06583141B1

Reaction notes

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