Sodium Hydroxide → HCID 67306614, compound

HRID 1013560Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH:21]2[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29]CC3C=CC=CC=3)=[O:28])[CH2:22]2)=[CH:8][S:9][C:10]=1[NH:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)=[O:5])[CH3:2].[OH-].[Na+]>CCO>[CH2:12]([CH:22]1[CH:21]([C:7]2[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:10]([NH:11][C:12](=[O:20])[C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)[S:9][CH:8]=2)[CH2:26][CH2:25][CH2:24][N:23]1[C:27]([OH:29])=[O:28])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 56 (96 mg, 0.19 mmol) in EtOH (5 ml) at room was added 1.0 N NaOH (aq.) (0.4 ml). The mixture was stirred at 60° C. for 2 hrs. The solvent was removed under vacuum. The residue was suspended in 1.0 N HCl (aq.) (2 ml) and extracted with ethyl acetate (3×5 ml). The combined organic layers were dried over anhydrous sodium sulfate. The drying agent was removed by filtration. The filtrate was concentrated under vacuum to give the crude product which was purified using preparative HPLC to give 57 (40.2 mg). 1H NMR (DMSO-d6) δ 1.44 (m, 1H), 1.51 (m, 1H), 1.73 (m, 1H), 2.01 (m, 1H), 2.88 (m, 2H), 4.03 (m, 1H), 4.21 (m, 1H), 5.10 (m, 2H), 6.87 (s, 1H), 7.36 (m, 5H), 7.54 (m, 1H), 7.68 (m, 2H), 7.75 (m, 1H), 12.58 (b, 1H), 13.74 (b, 1H) ppm.

Workup

customThe solvent was removed under vacuum
extractionextracted with ethyl acetate (3×5 ml)
dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
customThe drying agent was removed by filtration
concentrationThe filtrate was concentrated under vacuum
customto give the crude product which
customwas purified

Sources & evidence

ORD record: ord-5cbffe98e20b42f5999ac78e283bc9ed
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981925B2

Reaction notes

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