Water → HCID 25029151, compound

HRID 1644780Notes

Reaction equation

[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([C@H:13]([O:16][C@H:17]2[CH2:25][CH2:24][C@H:23]3[C@@H:19]([CH2:20][N:21]([C:26]4[CH2:30][CH2:29][C:28](=[O:31])[CH:27]=4)[CH2:22]3)[C@@H:18]2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[CH3:38])[CH2:14][OH:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[H-].[Na+].O.[CH3:44]N(C=O)C>IC>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C@H:13]([O:16][C@H:17]2[CH2:25][CH2:24][C@H:23]3[C@@H:19]([CH2:20][N:21]([C:26]4[CH2:30][CH2:29][C:28](=[O:31])[CH:27]=4)[CH2:22]3)[C@@H:18]2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[CH3:38])[CH2:14][O:15][CH3:44])[CH:4]=[C:3]([C:2]([F:39])([F:1])[F:40])[CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The compound from EXAMPLE 3 (0.02 g, 0.035 mmol) was dissolved in DMF (15 mL) and cooled to 0° C. NaH solid (12.8 mg, 0.07 mmol) was added, and the reaction mixture was stirred at 0° C. for 5 min. A few drops of iodomethane (excess) were added to the mixture. After stirring for another 10 min at 0° C., water (1 mL) was added and the water/DMF were removed in vacuo. The residue was taken into ethyl acetate. The mixture was washed with water, dried over magnesium sulfate and concentrated. The crude material was purified by preparative TLC (10% methanol in ethyl acetate) to afford the title compound. M++1: 582.47.

Workup

stirringAfter stirring for another 10 min at 0° C.
customthe water/DMF were removed in vacuo
washThe mixture was washed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe crude material was purified by preparative TLC (10% methanol in ethyl acetate)

Sources & evidence

ORD record: ord-d660f727e90748778068f0b07c0ee3b3
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08124633B2

Reaction notes

Loading…