Citric Acid → HCID 59533407, compound

HRID 925928Notes

Reaction equation

[Li+].[OH-].C[O:4][C:5](=[O:27])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([CH3:14])[C:7]=1[NH:15][C:16]([C:18]1[S:19][CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[N:22]=1)=[O:17].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CCO.O>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([C:5]([OH:27])=[O:4])=[C:7]([NH:15][C:16]([C:18]2[S:19][CH:20]=[C:21]([C:23]([F:26])([F:24])[F:25])[N:22]=2)=[O:17])[C:8]=1[CH3:14]

Participants

Conditions

Temperature: 60 °C

Procedure

LiOH (240 mg, 1.2 eq.) was added to a mixture of compound 204 (3 g, 1 eq.) in EtOH/H2O (20 mL/20 mL) at room temperature. The reaction mixture was stirred at 60° C. for 3 hrs and was allowed to cooled down to room temperature. A 5% aqueous solution of citric acid was added and the mixture was extracted with EtOAc. Organic phase was dried over MgSO4, filtered, and concentrated under reduced pressure to yield compound 205 as a white solid in 88% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 1.51 (s, 3H), 3.85 (s, 3H), 6.75 (d, J=8.75 Hz, 1H), 7.87 (d, J=8.75 Hz, 1H), 7.95 (s, 1H), 10.48 (s, 1H).

Workup

temperatureto cooled down to room temperature
extractionthe mixture was extracted with EtOAc
dry with materialOrganic phase was dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-91ca32188dad4399a27494445ad30610
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284307B2

Reaction notes

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