Lithium Hydroxide → 3-[3-Benzyl-4-(2-{4-[(tert-butoxycarbonyl)amino]phenyl}ethoxy)phenyl]-2-ethoxypropanoic acid

HRID 353309Notes

Reaction equation

HRID 353309 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([CH2:31][CH:32]([O:38][CH2:39][CH3:40])[C:33]([O:35]CC)=[O:34])[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+].C1COCC1.S([O-])(O)(=O)=O.[K+]>O.C(O)C>[CH2:1]([C:8]1[CH:9]=[C:10]([CH2:31][CH:32]([O:38][CH2:39][CH3:40])[C:33]([OH:35])=[O:34])[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:19][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 516920Potassium bisulfateHCID 22708452Ethyl 3-[3-benzyl-4-(2-{4-[(tert-butoxycarbonyl)amino]phenyl}ethoxy)phenyl]-2-ethoxypropanoate

Product 1

HCID 227084273-[3-Benzyl-4-(2-{4-[(tert-butoxycarbonyl)amino]phenyl}ethoxy)phenyl]-2-ethoxypropanoic acidYield 20%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Ethyl 3-[3-benzyl-4-(2-{4-[(tert-butoxycarbonyl)amino]phenyl}ethoxy)phenyl]-2-ethoxypropanoate (0.3 g, 0.5 mmol) and lithium hydroxide (0.015 g, 0.6 mmol) was added to a mixture of THF (10 ml), ethanol (2 ml) and water (2 ml). After stirring in room temperature for 5 h the mixture was acidified to pH 3 with saturated potassium hydrogen sulphate. Water was added and the mixture was extracted with ethylacetate. The organic layer was separated and evaporated. The residue was purified on silica gel using isooctane/ethylacetate/methanol 10:10:1. This yielded 70 mg (0.1 mmol) of the title product.

Workup

  1. extractionthe mixture was extracted with ethylacetate
  2. customThe organic layer was separated
  3. customevaporated
  4. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-74f1a0fcb15f40d890a071afbef6dc52
Source dataset
uspto-grants-2004_06
Patent number
US06750252B2

Reaction notes

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