Sodium Hydroxide → HCID 67306614, compound

HRID 387505Notes

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-7a9f19a7f1dd4f94a76cb9238a85f80a
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372991B2

Reaction notes

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