Hydrochloric Acid → HCID 178460984, compound

HRID 415989Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([Cl:17])[C:14]([CH2:18][C@@H:19]3[CH2:23][CH2:22][N:21]([C@H:24]4[CH2:29][CH2:28][C@@H:27]([O:30][Si:31]([CH:38]([CH3:40])[CH3:39])([CH:35]([CH3:37])[CH3:36])[CH:32]([CH3:34])[CH3:33])[CH2:26][CH2:25]4)[C:20]3=[O:41])=[C:13](Cl)[CH:12]=2)=[CH:7][CH:6]=1)=[O:4].C1COCC1.[OH-].[Li+].[ClH:50]>O.CO>[Cl:50][C:6]1[CH:7]=[C:8]([C:11]2[CH:16]=[C:15]([Cl:17])[C:14]([CH2:18][C@@H:19]3[CH2:23][CH2:22][N:21]([C@H:24]4[CH2:29][CH2:28][C@@H:27]([O:30][Si:31]([CH:38]([CH3:40])[CH3:39])([CH:32]([CH3:33])[CH3:34])[CH:35]([CH3:36])[CH3:37])[CH2:26][CH2:25]4)[C:20]3=[O:41])=[CH:13][CH:12]=2)[CH:9]=[CH:10][C:5]=1[C:3]([OH:2])=[O:4]

Participants

Conditions

Temperature: 1 °C

Procedure

Stir a mixture of 3′,5′-dichloro-4′-[(R)-2-oxo-cis-1-(4-triisopropylsilanyloxy-cyclohexyl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid methyl ester (35.6 g, 56.26 mmol), 150 mL THF and 100 mL methanol under nitrogen in an ice/water bath. Add a solution of lithium hydroxide (4.04 g, 168.79 mmol) in 100 mL water. Stir the mixture 4 hr at RT. Cool the solution to about 1° C. in an ice/acetone bath, dilute with 500 mL water, then adjust the pH to about 2-3 with 0.5 M aqueous hydrochloric acid. Extract with ethyl acetate (3×150 mL), wash with 100 mL each, water and brine then dry over magnesium sulfate. Filter, and concentrate to 34.6 g (99%) of a foam.

Workup

stirringStir the mixture 4 hr at RT
extractionExtract with ethyl acetate (3×150 mL)
washwash with 100 mL each, water and brine
dry with materialthen dry over magnesium sulfate
filtrationFilter
concentrationconcentrate to 34.6 g (99%) of a foam

Sources & evidence

ORD record: ord-8e803d2b173a4d70b3e2317675259573
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088776B2

Reaction notes

Loading…