Lithium Hydroxide → (R)-3',5'-Dichloro-4'-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic Acid

HRID 1692084Notes

Reaction equation

HRID 1692084 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]([N:24]4[CH2:29][CH2:28][CH: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:42])[CH:12]=2)=[CH:7][CH:6]=1)=[O:4].[Li+].[OH-]>C1COCC1.CO>[Cl:17][C:15]1[CH:16]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=2)[CH:12]=[C:13]([Cl:42])[C:14]=1[CH2:18][C@@H:19]1[CH2:23][CH2:22][N:21]([N:24]2[CH2:25][CH2:26][CH:27]([O:30][Si:31]([CH:32]([CH3:33])[CH3:34])([CH:38]([CH3:40])[CH3:39])[CH:35]([CH3:37])[CH3:36])[CH2:28][CH2:29]2)[C:20]1=[O:41]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66904939(R)-3',5'-dichloro-4'-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid methyl ester

Product 1

HCID 66904943(R)-3',5'-Dichloro-4'-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic AcidYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Treat a solution of (R)-3′,5′-dichloro-4′-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid methyl ester (0.36 g) in THF (5 mL) and methanol (2 mL) with 2N LiOH (5 mL) and stir at room temperature for 3 hours. Partition the mixture between ethyl acetate (25 mL) and 1 N HCl (10 mL). Dry the organic layer (Na2SO4) and remove the solvent in vacuo to afford 0.34 g (97%) of the title compound. MS (m/z): 619 (M+).

Workup

  1. customPartition the mixture between ethyl acetate (25 mL) and 1 N HCl (10 mL)
  2. dry with materialDry the organic layer (Na2SO4)
  3. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-922fec1e14014e0ea014fd6023a0b969
Source dataset
uspto-grants-2012_04
Patent number
US08153807B2

Reaction notes

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