Sodium Hydroxide → HCID 178445643, compound

HRID 1633895Notes

Reaction equation

C([O:3][C:4](=[O:42])[CH2:5][CH2:6][NH:7][C:8](=[O:41])[C:9]1[CH:14]=[CH:13][C:12]([CH:15]([NH:26][C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=2)=[O:28])[C@H:16]2[CH2:21][CH2:20][C@@H:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)C.[OH-].[Na+]>C(O)C>[C:22]([C@@H:19]1[CH2:20][CH2:21][C@H:16]([CH:15]([NH:26][C:27]([NH:29][C:30]2[CH:31]=[CH:32][C:33]([O:36][C:37]([F:38])([F:39])[F:40])=[CH:34][CH:35]=2)=[O:28])[C:12]2[CH:13]=[CH:14][C:9]([C:8]([NH:7][CH2:6][CH2:5][C:4]([OH:42])=[O:3])=[O:41])=[CH:10][CH:11]=2)[CH2:17][CH2:18]1)([CH3:25])([CH3:23])[CH3:24]

Participants

Conditions

Temperature: 20 °C

Procedure

3-{4-[1-(cis-4-tert-Butylcyclohexyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoylamino}-propionic acid ethyl ester (0.2 g, 0.3 mmol) was suspended in ethanol (8 mL) and sodium hydroxide (4N, 0.6 mL) added. The reaction mixture was stirred for 16 hours at 20° C. and then concentrated in vacuo until all ethanol was removed. The reaction mixture was diluted with water (50 mL) and adjusted to pH 2 with hydrochloric acid (4N). The aqueous phase was extracted with ethyl acetate (80 mL) and the organic phase was dried (MgSO4) and concentrated in vacuo to give the title compound.

Workup

concentrationconcentrated in vacuo until all ethanol
customwas removed
additionThe reaction mixture was diluted with water (50 mL)
extractionThe aqueous phase was extracted with ethyl acetate (80 mL)
dry with materialthe organic phase was dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1c34132d5db142b197dcc60d44b873e6
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503949B1

Reaction notes

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