Methanol → 18-Hydroxy-14-(4-methoxy-benzyl)-2,15-dioxo-3,14,16-triaza-tricyclo-[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid ethyl ester

HRID 570121Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]12[CH2:24][CH:23]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[C:14](=[O:34])[N:13]1[CH:9]([CH2:10][CH:11]([O:35]C(=O)C3C=CC([N+]([O-])=O)=CC=3)[CH2:12]1)[C:8](=[O:47])[NH:7]2)=[O:5])[CH3:2].CO.O.[Li+].[OH-]>C1COCC1.CC(O)=O>[CH2:1]([O:3][C:4]([C:6]12[CH2:24][CH:23]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[C:14](=[O:34])[N:13]1[CH:9]([CH2:10][CH:11]([OH:35])[CH2:12]1)[C:8](=[O:47])[NH:7]2)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Crude compound 26 (445 mg) was dissolved in THF (20 ml), MeOH (10 ml) and water (10 ml). After cooling to 0° C. 1M LiOH (2 ml) was added. After 1.5 h the hydrolysis was completed and HOAc (1 ml) was added and the solution was evaporated to appr 10 ml. Water was added and the mixture was extracted with DCM (2×30 ml). The pooled organic phase was washed with NaHCO3 (aq), water, brine and dried over MgSO4. The crude product was purified by column chromatography on silica (DCM/MeOH: 100/0-80/20) to give the title compound (201 mg, 67%).

Workup

customthe solution was evaporated
additionWater was added
extractionthe mixture was extracted with DCM (2×30 ml)
washThe pooled organic phase was washed with NaHCO3 (aq), water, brine
dry with materialdried over MgSO4
customThe crude product was purified by column chromatography on silica (DCM/MeOH: 100/0-80/20)

Sources & evidence

ORD record: ord-e047d2f9019d44f1b8113f8cbee29f22
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023808B2

Reaction notes

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