Sodium Hydroxide → HCID 11452274, compound

HRID 915793Notes

Reaction equation

C([O:4][CH:5]([CH:9]([O:32]C(=O)C)[C:10]([NH:12][CH2:13][C:14]1[CH:27]=[CH:26][C:25]2[O:24][C:23]3[C:18]4=[C:19]([C:28](=[O:31])[NH:29][N:30]=[C:17]4[C:16]=2[CH:15]=1)[CH:20]=[CH:21][CH:22]=3)=[O:11])[C:6]([OH:8])=[O:7])(=O)C.[OH-].[Na+]>O.O1CCOCC1>[OH:4][CH:5]([CH:9]([OH:32])[C:10]([NH:12][CH2:13][C:14]1[CH:27]=[CH:26][C:25]2[O:24][C:23]3[C:18]4=[C:19]([C:28](=[O:31])[NH:29][N:30]=[C:17]4[C:16]=2[CH:15]=1)[CH:20]=[CH:21][CH:22]=3)=[O:11])[C:6]([OH:8])=[O:7]

Participants

Conditions

Temperature: 40 °C

Procedure

Compound 51 was dissolved in a solution of NaOH (2.5 equivalent) in H2O/Dioxane. The reaction mixture was stirred overnight at 40° C., then was acidified to pH=3. Aqueous layer was extracted with ethyl acetate. Organic layer was dried with MgSO4. Solvent was removed in vacuo to afford a white solid 52 in 25% yield. MS: (ES+): 398; Mp: 181-185° C.; 1H-NMR (DMSO-d6, 400 MHz): 12.54 (s, 1H), 8.32 (t, J=6.2 Hz, 1H), 7.93 (d, J=2.0 Hz, 1H), 7.90-7.80 (m, 2H), 7.62 (dd, J=7.5 and 2.0 Hz, 1H), 7.40 (dd, J=8.5 and 2.0 Hz, 1H), 7.25 (d, J=8.5 Hz, 1H), 4.30-4.19 (m, 4H); Anal. Calcd for C19H15N3O7.(3H2O): C, 50.56; H, 4.69; N, 9.31. Found: C, 50.59; H, 4.07; N, 9.28.

Workup

extractionAqueous layer was extracted with ethyl acetate
dry with materialOrganic layer was dried with MgSO4
customSolvent was removed in vacuo

Sources & evidence

ORD record: ord-e5e0ac0c98c84128949394c6021d8cc5
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268138B2

Reaction notes

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