Tetrahydrofuran → HCID 67504216, compound

HRID 19332Notes

Reaction equation

C[O:2][C:3](=[O:29])[C@@H:4]([N:15]1[CH2:19][C:18]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])=[CH:17][C:16]1=[O:28])[CH2:5][CH2:6][O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].O1CCCC1.O.[OH-].[Li+]>O>[C:11]([Si:8]([CH3:10])([CH3:9])[O:7][CH2:6][CH2:5][C@H:4]([N:15]1[CH2:19][C:18]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])=[CH:17][C:16]1=[O:28])[C:3]([OH:29])=[O:2])([CH3:13])([CH3:12])[CH3:14]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of (S)-4-(t-butyl-dimethyl-silanyloxy)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-butyric acid methyl ester (250 mg, 0.57 mmol) in a 1:1 solution of tetrahydrofuran:water (8 mL) was treated with lithium hydroxide monohydrate (48 mg, 1.14 mmol) and stirred for 1.5 h at 25° C. After such time, the mixture was concentrated in vacuo to remove the tetrahydrofuran and diluted with water (10 mL) and the pH adjusted to pH=5 with 1N aqueous hydrochloric acid and extracted with ethyl acetate. The organic layers were then dried and concentrated in vacuo to afford (S)-4-(t-butyl-dimethyl-silanyloxy)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-butyric acid (195 mg, 81%) as an off-white foam: HR-ES-MS m/z calculated for C20H28NO5ClSi [M+H]+ 426.1498, observed 426.1498.

Workup

concentrationAfter such time, the mixture was concentrated in vacuo
customto remove the tetrahydrofuran
additiondiluted with water (10 mL)
extractionextracted with ethyl acetate
customThe organic layers were then dried
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f860931f98fe470faeae7909d1f133a1
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

Loading…