Ethanol → (5-tert-Butyl-4-{4-hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl}-2-methyl-phenoxy)-acetic acid ethyl ester

HRID 356548노트

반응식

HRID 356548 반응식
[OH:1][C:2]1[CH2:7][C:6]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[O:5][C:4](=[O:26])[CH:3]=1.[C:27]([C:31]1[C:32]([S:43]S(C2C=CC(C)=CC=2)(=O)=O)=[CH:33][C:34]([CH3:42])=[C:35]([CH:41]=1)[O:36][CH2:37][C:38]([OH:40])=[O:39])([CH3:30])([CH3:29])[CH3:28].C([O-])([O-])=O.[K+].[K+].CN(C=O)C.[CH3:65][CH2:66]O>>[CH2:65]([O:40][C:38](=[O:39])[CH2:37][O:36][C:35]1[CH:41]=[C:31]([C:27]([CH3:28])([CH3:29])[CH3:30])[C:32]([S:43][C:3]2[C:4](=[O:26])[O:5][C:6]([CH2:17][CH2:18][C:19]3[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=3)([CH2:8][CH2:9][C:10]3[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=3)[CH2:7][C:2]=2[OH:1])=[CH:33][C:34]=1[CH3:42])[CH3:66]

참가 물질

6

반응물 5

HCID 702EthanolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 18798672[5-tert-Butyl-2-methyl-4-(toluene-4-sulfonylsulfanyl)-phenoxy]-acetic acidHCID 546822654-Hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

생성물 1

HCID 70253780(5-tert-Butyl-4-{4-hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl}-2-methyl-phenoxy)-acetic acid ethyl ester

실험 절차

The title compound was synthesized via General Method 9 using 209 mg (0.6 mmol) of 4-hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one (prepared in Example PP), 250 mg (0.6 mmol) of [5-tert-butyl-2-methyl-4-(toluene-4-sulfonylsulfanyl)-phenoxy]-acetic acid (prepared in Example NNNN), 327 mg (2.4 mmol) of K2CO3, and DMF (2 mL). The reaction was conducted in EtOH to effect ester exchange. The reaction was worked up as described. The residue was chromatographed on silica gel eluting with (1:1 CH2Cl2 :EtOAc+2% MeOH) to yield the product, m.p. 162°-163° C. 1H NMR (DMSO-d6) δ 1.21 (t, 3 H), 1.47 (s, 9 H), 1.8 (s, 3 H), 2.0 (m, 4 H), 2.6 (m, 6 H), 2.95 (s, 2 H), 4.25 (q, 2 H), 4.75 (s, 2 H), 6.65 (m, 5 H), 6.75 (s, 1 H), 7.0 (d 4 H), 9.18 (s, 2 H).

후처리

  1. customThe residue was chromatographed on silica gel eluting with (1:1 CH2Cl2 :EtOAc+2% MeOH)
  2. customto yield the product, m.p. 162°-163° C

출처 및 근거

ORD 기록
ord-1001d449b03b456b9ecd6bbf03c73de2
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834506

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