Potassium Carbonate → HCID 54688364, 화합물

HRID 356562노트

반응식

HRID 356562 반응식
[OH:1][C:2]1[CH2:7][C@@:6]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)([CH:8]([CH3:10])[CH3:9])[O:5][C:4](=[O:20])[CH:3]=1.[NH2:21][C:22]1[C:27]([CH3:28])=[CH:26][C:25]([S:29]S(C2C=CC(C)=CC=2)(=O)=O)=[C:24]([C:40]([CH3:43])([CH3:42])[CH3:41])[CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:21][C:22]1[C:27]([CH3:28])=[CH:26][C:25]([S:29][C:3]2[C:4](=[O:20])[O:5][C:6]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)([CH:8]([CH3:10])[CH3:9])[CH2:7][C:2]=2[OH:1])=[C:24]([C:40]([CH3:43])([CH3:42])[CH3:41])[CH:23]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 10569823Toluene-4-thiosulfonic acid S-(4-amino-2-tert-butyl-5-methyl-phenyl) esterHCID 54682331(S)-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one

생성물 1

HCID 54688364HCID 54688364, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The title compound was prepared as described in General Method 9 using 3.0 g (10.86 mmol) of (S)-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one (prepared in Example WWWW), 3.98 g (11.40 mmol) of toluene-4-thiosulfonic acid S-(4-amino-2-tert-butyl-5-methyl-phenyl) ester (prepared in Example HHHH), 4.50 g of anhydrous K2CO3 and 54 mL DMF. The reaction was stirred at room temperature overnight. The reaction was quenched with saturated NH4Cl solution and extracted with EtOAc. The organic phase was dried over MgSO4 and concentrated. The crude material was purified by flash silica gel chromatography, eluting with EtOAc, to give the title compound, m.p. 147°-149° C. (dec.). 1H-NMR (DMSO-d6) δ 0.89 (d, 3 H), 0.93 (d, 3 H), 1.42 (s, 9 H), 1.71 (s. 3 H), 1.85-1.93 (m, 2 H), 2.15 (m, 1 H), 2.41-2.50 (m, 2 H, partially obscured by DMSO), 2.67 (d of ABX q, 1 H), 2.89 (d of ABX q, 1 H), 6.55 (s, 1 H), 6.60 (s, 1 H), 6.64 (d, 2H), 6.93 (d, 2H), 9.13 (br s, 1 H).

후처리

  1. customThe title compound was prepared
  2. customThe reaction was quenched with saturated NH4Cl solution
  3. extractionextracted with EtOAc
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude material was purified by flash silica gel chromatography
  7. washeluting with EtOAc

출처 및 근거

ORD 기록
ord-c4619de1b1ad4028b0623f9b40a7541e
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834506

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