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

HRID 1178569노트

반응식

HRID 1178569 반응식
[F: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>[F: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 86600806HCID 86600806, 화합물

생성물 1

HCID 103115412-{[2-(4-Fluorophenyl)ethyl]thio}-3-[4-(2-{4-[(methylsulfonyl)oxy]-phenoxy}ethyl)phenyl]propanoic acid수율 33.1%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

Methyl 2-{[2-(4-fluorophenyl)ethyl]thio}-3-[4-(2-{4-[(methylsulfonyl)oxy]-phenoxy}ethyl)phenyl]propanoate (77 mg, 0.14 mmol) was dissolved in 2.5 ml of a 4:1 mixture of THF and water and cooled on an ice-bath. Lithium hydroxide (6.9 mg, 0.29 mmol) was added. Water was added after 2 days of stirring at room temperature. The THF was evaporated under reduced pressure. The aqueous phase was acidified with 1M HCl and extracted with EtOAc three times. 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). 24 mg of the desired product (yield 30%) was obtained as an oil.

후처리

  1. temperaturecooled on an ice-bath
  2. customThe THF was evaporated under reduced pressure
  3. extractionextracted with EtOAc three times
  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-8d6bc0a54b66457da1fd6c1597e5dcba
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276539B2

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