Potassium Carbonate → 3-(4-Amino-2-tert-butyl-5-methylphenylsulfanyl)-4-hydroxy-6,6-bis[2-(4-hydroxyphenyl)ethyl]-5,6-dihydropyran-2-one

HRID 356549노트

반응식

HRID 356549 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.[NH2:27][C:28]1[C:33]([CH3:34])=[CH:32][C:31]([S:35]S(C2C=CC(C)=CC=2)(=O)=O)=[C:30]([C:46]([CH3:49])([CH3:48])[CH3:47])[CH:29]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:27][C:28]1[C:33]([CH3:34])=[CH:32][C:31]([S:35][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])=[C:30]([C:46]([CH3:49])([CH3:48])[CH3:47])[CH:29]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 10569823Toluene-4-thiosulfonic acid S-(4-amino-2-tert-butyl-5-methyl-phenyl) esterHCID 546822654-Hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

생성물 1

HCID 546822773-(4-Amino-2-tert-butyl-5-methylphenylsulfanyl)-4-hydroxy-6,6-bis[2-(4-hydroxyphenyl)ethyl]-5,6-dihydropyran-2-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The compound was synthesized following General Method 9 using 118 mg (0.33 mmol) of 4-hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one (prepared in Example PP), 150 mg (0.33 mmol) of toluene-4-thiosulfonic acid S-(4-amino-2-tert-butyl-5-methyl-phenyl) ester (prepared in Example HHHH), 184 mg (1.32 mmol) of K2CO3 and 2 mL of DMF. The reaction was worked up by partitioning between EtOAc and H2O. The organic layer was separated and concentrated, then triturated with Et2O. The resultant solid was placed in chilled HCl-saturated CH2Cl2 and stirred for 18 hours. After concentration, the residue was triturated with Et2O to yield the title compound, m.p. 140°-145° C. 1H NMR (DMSO-d6) δ 1.5 (s, 9 H), 1.9 (s, 3 H), 2.05 (m, 4 H), 2.5 (m, 6 H), 6.68 (d, 4 H), 6.75 (s, 1 H), 7.0 (d, 4 H), 7.35 (s, 1 H), 7.95 (s, 2 H), 9.25 (s, 2 H).

후처리

  1. customThe compound was synthesized
  2. customby partitioning between EtOAc and H2O
  3. customThe organic layer was separated
  4. concentrationconcentrated
  5. customtriturated with Et2O
  6. concentrationAfter concentration
  7. customthe residue was triturated with Et2O

출처 및 근거

ORD 기록
ord-6392d600b38741e1ae6f94b3b603f04a
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834506

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