Lithium Hydroxide → HCID 118116930, compound

HRID 2279940Notes

Reaction equation

HRID 2279940 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:18]=1)[C:13]([O:15]C)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>CO.O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:18]=1)[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 118117725HCID 118117725, compound

Product 1

HCID 118116930HCID 118116930, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-(benzyloxycarbonylamino)-2-(3-benzyloxyphenyl)acetate (640 mg, 1.75 mmol) and aqueous lithium hydroxide (1 N, 3.50 mL, 3.50 mmol) in methanol (5 mL) and tetrahydrofuran (5 mL) was stirred at room temperature for one hour. The mixture was concentrated in vacuo and the residue diluted with dichloromethane (30 mL) and acidified to pH 0.5 with 2 N HCl. The aqueous phase was re-extracted with dichloromethane (2×50 mL). The combined organic fractions were dried over a hydrophobic frit and the solvent was removed in vacuo to give the title compound as a light brown oil (460 mg, 67%). This was used in the next step without further purification.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue diluted with dichloromethane (30 mL)
  3. extractionThe aqueous phase was re-extracted with dichloromethane (2×50 mL)
  4. customThe combined organic fractions were dried over a hydrophobic frit
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ad9b8152567846b7bd827a5bffc34968
Source dataset
uspto-grants-2015_09
Patent number
US09133185B2

Reaction notes

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