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Citric Acid → 3-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-5-[(phenylmethyl)oxy]benzoic acid

HRID 548648
Notes
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Reaction equation

HRID 548648 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]([CH3:30])[O:11][C:12]1[CH:13]=[C:14]([CH:19]=[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=1)[C:15]([O:17]C)=[O:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O.O.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[C:24]1([CH2:23][O:22][C:20]2[CH:19]=[C:14]([CH:13]=[C:12]([O:11][C@@H:10]([CH3:30])[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])[CH:21]=2)[C:15]([OH:17])=[O:16])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962Water2×HCID 168937Lithium hydroxide, monohydrateHCID 59127165Methyl 3-((s)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[(phenylmethyl)oxy]benzoate

Product 1

HCID 536296343-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-5-[(phenylmethyl)oxy]benzoic acid
Yield 88.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

Methyl 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[(phenylmethyl)oxy]benzoate (3.0 g, 6.98 mmol) was dissolved in THF (50 mL) and water (10 mL) and lithium hydroxide monohydrate (586 mg, 13.95 mmol) added. The resultant mixture was heated with stirring at 45° C. for 2 hours, then at ambient temperature for 16 hours, and at 45° C. for a further 4 hours. Water (40 mL) was added and the solvent removed in vacuo. The resultant solution was acidified carefully with 1M citric acid (2 equivalents), washed with water and brine then dried (MgSO4), filtered and evaporated in vacuo to give the title compound as a colourless gum (2.58 g).

Workup

  1. waitat ambient temperature for 16 hours
  2. waitat 45° C. for a further 4 hours
  3. customthe solvent removed in vacuo
  4. washwashed with water and brine
  5. dry with materialthen dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-53255cda81cf4972872396b3a3987613
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07943607B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes