Lithium Hydroxide → 2-{[2-(4-Hydroxyphenyl)ethyl]thio}-3-[4-(2-{4-[(methylsulfonyl)oxy]-phenoxy}ethyl)phenyl]propanoic acid

HRID 33817노트

반응식

HRID 33817 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][S:10][CH:11]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][S:33]([CH3:36])(=[O:35])=[O:34])=[CH:28][CH:27]=3)=[CH:19][CH:18]=2)[C:12]([O:14]C)=[O:13])=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][S:10][CH:11]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][O:25][C:26]3[CH:27]=[CH:28][C:29]([O:32][S:33]([CH3:36])(=[O:35])=[O:34])=[CH:30][CH:31]=3)=[CH:19][CH:18]=2)[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 73017203Methyl 2-{[2-(4-hydroxyphenyl)ethyl]thio}-3-[4-(2-{4-[(methylsulfonyl)oxy]phenoxy}ethyl)phenyl]propanoate

생성물 1

HCID 102179842-{[2-(4-Hydroxyphenyl)ethyl]thio}-3-[4-(2-{4-[(methylsulfonyl)oxy]-phenoxy}ethyl)phenyl]propanoic acid수율 97%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

Methyl 2-{[2-(4-hydroxyphenyl)ethyl]thio}-3-[4-(2-{4-[(methylsulfonyl)oxy]phenoxy}-ethyl)phenyl]propanoate (105 mg, 0.2 mmol) was dissolved in 6.5 ml of a 7:1 mixture of THF and water and cooled on an ice-bath Lithium hydroxide (9.4 mg, 0.4 mmol ) was added. Water was added to the reaction mixture after 24 hours of stirring at room temperature. The THF was evaporated under reduced pressure and the residue was acidified with 1M hydrochloric acid. The water phase was extracted with EtOAc (×3), the organic phases were pooled, washed (water, brine), dried (MgSO4) and evaporated. The crude product was purified using preparative HPLC (eluent: CH3CN/5% CH3CN-waterphase containing 0.1M NH4OAc) to give 74 mg of the desired product (yield 97%) as an oil.

후처리

  1. additionwas added
  2. customThe THF was evaporated under reduced pressure
  3. extractionThe water phase was extracted with EtOAc (×3)
  4. washwashed (water, brine)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was purified
  8. additionHPLC (eluent: CH3CN/5% CH3CN-waterphase containing 0.1M NH4OAc)

출처 및 근거

ORD 기록
ord-e386fa318ab34549940f2485a73ff957
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429675B2

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