Hydrochloric Acid → 5-{[2-Tert-butyl-4-(2-hydroxyethoxy)-5-methylphenyl]sulfanyl}-6-hydroxy-2-[4-(2-hydroxyethoxy)phenyl]-2-(2-phenylethyl)-2,3-dihydro-4h-pyran-4-one

HRID 1003908노트

반응식

HRID 1003908 반응식
C([Si](C)(C)[O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:21][C:20](=[O:22])[CH:19]=[C:18]([OH:23])[CH2:17]2)=[CH:12][CH:11]=1)(C)(C)C.[C:34]([C:38]1[CH:43]=[C:42]([O:44][CH2:45][CH2:46][O:47][Si](C(C)(C)C)(C)C)[C:41]([CH3:55])=[CH:40][C:39]=1[S:56]S(C1C=CC(C)=CC=1)(=O)=O)([CH3:37])([CH3:36])[CH3:35].C([O-])([O-])=O.[K+].[K+].Cl>CO.CN(C=O)C>[C:34]([C:38]1[CH:43]=[C:42]([O:44][CH2:45][CH2:46][OH:47])[C:41]([CH3:55])=[CH:40][C:39]=1[S:56][C:19]1[C:20](=[O:22])[O:21][C:16]([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][OH:6])=[CH:11][CH:12]=2)([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:17][C:18]=1[OH:23])([CH3:37])([CH3:36])[CH3:35]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 10791774Toluene-4-thiosulfonic acid S-{2-tert-butyl-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-methyl-phenyl}esterHCID 546822666-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-4-hydroxy-6-phenethyl-5,6-dihydro-pyran-2-one

생성물 1

HCID 546822895-{[2-Tert-butyl-4-(2-hydroxyethoxy)-5-methylphenyl]sulfanyl}-6-hydroxy-2-[4-(2-hydroxyethoxy)phenyl]-2-(2-phenylethyl)-2,3-dihydro-4h-pyran-4-one

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

To a round bottom flask equipped with a magnetic stirrer were added 6-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl} -4-hydroxy-6-phenethyl-5,6-dihydro-pyran-2-one (prepared in Example SS; 0.260 g, 0.555 mmol), toluene-4-thiosulfonic acid S-{2-tert-butyl-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-methyl-phenyl) ester (prepared in Example PPP; 0.282 g, 0.555 mmol), K2CO3 (0.346 g, 2.50 mmol), and DMF (5 mL), as described in General Method 9. The mixture was stirred at room temperature for 2 days at which time MeOH (150 mL) was added and the solution taken to pH 3.0 with conc. HCl. The reaction was quenched with H2O (500 mL) and extracted with EtOAc. The organics were dried over MgSO4 and concentrated; the residue was taken up in a small amount of EtOAc and triturated with hexane. The solid was filtered and dried under high vacuum to yield the title compound, m.p. >190° C. (dec.). 1H NMR (DMSO-d6) δ 1.45 (s, 9 H), 1.68 (s, 3 H), 2.22 (br m, 4 H), 2.51 (br m, partially obscured by DMSO, 2 H), 3.34 (d of ABX q, partially obscured by H2 0, 1 H), 3.40 (d of ABX q, partially obscured by H2O, 1 H), 3.67 (br m, 2 H), 3.72 (br m, 2 H)3.91 (t, 2 H), 3.98 (t, 2 H), 6.76 (s, 1 H), 6.96 (s, 1 H), 6.99 (d, 2 H), 7.08-7.22 (m, 1 H), 7.10 (d, 2 H), 7.24 (d, 2 H), 7.30 (d, 2 H).

후처리

  1. customTo a round bottom flask equipped with a magnetic stirrer
  2. additionwas added
  3. customThe reaction was quenched with H2O (500 mL)
  4. extractionextracted with EtOAc
  5. dry with materialThe organics were dried over MgSO4
  6. concentrationconcentrated
  7. customtriturated with hexane
  8. filtrationThe solid was filtered
  9. customdried under high vacuum

출처 및 근거

ORD 기록
ord-630f97ae53c1485a8919d7ab0e815975
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06046355

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