Ethanol → HCID 178445755, 화합물

HRID 1036383

반응식

HRID 1036383 반응식
[CH2:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C@:22]2([CH3:28])[CH2:26][O:25]C(=O)[NH:23]2)[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[OH-].[Li+].C(O)C.O>>[NH2:23][C@@:22]([C:17]1[CH:16]=[CH:15][C:14]2[C:19](=[CH:20][CH:21]=[C:12]([O:11][C@H:8]3[CH2:7][CH2:6][C@@H:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:10][CH2:9]3)[CH:13]=2)[CH:18]=1)([CH3:28])[CH2:26][OH:25]

참가 물질

5

반응물 4

HCID 702EthanolHCID 962WaterHCID 3939Lithium HydroxideHCID 178445732HCID 178445732, 화합물

생성물 1

HCID 178445755HCID 178445755, 화합물

실험 절차

The mixture of (R)-4-(6-(cis-4-butylcyclohexyloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one (294.3 mg, 0.7714 mmol) and lithium hydroxide (203 mg, 8.48 mmol) in Ethanol (4.9 mL, 0.084 mol) and water (1.6 mL, 9.1 mmol) was heated to reflux for overnight. LCMS showed reaction completed. The solvent was removed under vacuum and the residue was partitioned between water and CH2Cl2. The aqueous was extensively extracted with CH2Cl2. And the combined organic phase was dried over Na2SO4. The concentrated residue was taken up into CH2Cl2 and subjected to chromatography purification with CH2Cl2/MeOH (10:90 to 80:20) to give the product. LCMS 339.53 ([M−NH2]+, 100%). 1H NMR (400 MHz, CD3OD) δ ppm 0.92 (t, J=7.0 Hz, 3H), 1.21-1.50 (m, 9H), 1.54 (s, 3H), 1.56-1.71 (m, 4H), 2.05 (brd, J=13.3 Hz, 2H), 3.71 (AB, J=10.8 Hz, 2H), 4.69 (brs, 1H), 7.14 (dd, J=8.8, 3.3 Hz, 1H), 7.19 (s, 1H), 7.53 (d, J=8.7 Hz, 1H), 7.72 (d, J=8.7 Hz, 1H), 7.76 (d, J=8.7 Hz, 1H), 7.83 (s, 1H).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for overnight
  3. customreaction
  4. customThe solvent was removed under vacuum
  5. customthe residue was partitioned between water and CH2Cl2
  6. extractionThe aqueous was extensively extracted with CH2Cl2
  7. dry with materialAnd the combined organic phase was dried over Na2SO4
  8. customsubjected to chromatography purification with CH2Cl2/MeOH (10:90 to 80:20)
  9. customto give the product

출처 및 근거

ORD 기록
ord-617d8c49d46644f4af29d5a7b0e4b663
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546359B2

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