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

HRID 548648

반응식

HRID 548648 반응식
[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

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 962Water2회HCID 168937Lithium hydroxide, monohydrateHCID 59127165Methyl 3-((s)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[(phenylmethyl)oxy]benzoate

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
45 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-53255cda81cf4972872396b3a3987613
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943607B2

연결된 노트

불러오는 중…