Hydrochloric Acid → HCID 68884512, compound

HRID 1294287Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH2:28][C:29]1[N:30]=[C:31]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:32][C:33]=1[CH3:34])[C:9]1[CH:27]=[CH:26][C:12]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:21][C:22]([O:24]C)=[O:23])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.[OH-].[Na+].Cl>O.CO>[C:1]([O:5][C:6]([N:8]([CH2:28][C:29]1[N:30]=[C:31]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[O:32][C:33]=1[CH3:34])[C:9]1[CH:27]=[CH:26][C:12]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:21][C:22]([OH:24])=[O:23])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of methyl 2-[2-[4-[(t-butoxycarbonyl)[(5-methyl-2-phenyl-4-oxazolyl)methyl]amino]benzyloxy]phenyl]acetate (0.30 g), tetrahydrofuran (1.0 mL) and methanol (1.0 mL) was added a 1N aqueous sodium hydroxide solution (1.0 mL) and the mixture was stirred at 50° C. for 1 hr. 1N Hydrochloric acid (1.0 mL) and water were added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give 2-[2-[4-[(t-butoxycarbonyl)[(5-methyl-2-phenyl-4-oxazolyl)methyl]amino]benzyloxy]phenyl]acetic acid as a colorless amorphous compound (0.19 g, 66%).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-91b20e6ea4fa4d6587746933b90346c5
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238716B2

Reaction notes

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