Hydrochloric Acid → 4-[(4E)-3-[2-(4-Carboxyphenyl)ethyl]-5-{5-fluoro-2-[3-(2-oxopyrrolidin-1-yl)propoxy]phenyl}-pent-4-en-1-yl]benzoic acid

HRID 1512221Notes

Reaction equation

[OH-].[Li+].[F:3][C:4]1[CH:5]=[CH:6][C:7]([O:37][CH2:38][CH2:39][CH2:40][N:41]2[CH2:45][CH2:44][CH2:43][C:42]2=[O:46])=[C:8](/[CH:10]=[CH:11]/[CH:12]([CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([O:35]C)=[O:34])=[CH:29][CH:28]=2)[CH2:13][CH2:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=2)[CH:9]=1.Cl>C1COCC1.O>[C:19]([C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][CH:12](/[CH:11]=[CH:10]/[C:8]2[CH:9]=[C:4]([F:3])[CH:5]=[CH:6][C:7]=2[O:37][CH2:38][CH2:39][CH2:40][N:41]2[CH2:45][CH2:44][CH2:43][C:42]2=[O:46])[CH2:25][CH2:26][C:27]2[CH:28]=[CH:29][C:30]([C:33]([OH:35])=[O:34])=[CH:31][CH:32]=2)=[CH:24][CH:23]=1)([OH:21])=[O:20]

Participants

Conditions

Temperature: 50 °C

Procedure

18 mg (0.75 mmol) of lithium hydroxide are added to a solution of 150 mg (0.25 mmol) of methyl 4-[(4E)-5-{5-fluoro-2-[3-(2-oxopyrrolidin-1-yl)propoxy]phenyl}-3-{2-[4-(methoxycarbonyl)-phenyl]ethyl}pent-4-en-1-yl]benzoate in 10 ml of THF and 10 ml of water, and the mixture is stirred at 50° C. for 12 h. The mixture is then adjusted to pH 2 using 1 M hydrochloric acid and concentrated. The residue obtained is purified directly by preparative HPLC. This gives 130 mg (content 96%, 0.22 mmol, 87% of theory) of the title compound.

Workup

concentrationconcentrated
customThe residue obtained
customis purified directly by preparative HPLC

Sources & evidence

ORD record: ord-4965c160ed33491a83c841744d8a7eaf
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217063B2

Reaction notes

Loading…