Isovaleryl chloride → HCID 52911545, compound

HRID 73615Notes

Reaction equation

HRID 73615 reaction equation
[C:1]1([NH:7][CH:8]2[C@:17]3([OH:18])[C@H:12]([CH2:13][CH2:14][CH2:15][CH2:16]3)[NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(O)=O.[Na+].[CH3:24][CH:25]([CH3:30])[CH2:26][C:27](Cl)=[O:28]>C(Cl)Cl>[OH:18][C@:17]12[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]1[N:11]([C:27](=[O:28])[CH2:26][CH:25]([CH3:30])[CH3:24])[CH2:10][CH2:9][CH:8]2[NH:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 66054Isovaleryl chlorideHCID 516892Sodium BicarbonateHCID 68154084HCID 68154084, compound

Product 1

HCID 52911545HCID 52911545, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (4aR,8aS)-4-(phenylamino)octahydroquinolin-4a(2H)-ol (20 mg, 0.081 mmol) in 1:1 CH2Cl2:sat'd. aq. NaHCO3 (3 mL) was added 3-methylbutanoyl chloride (0.049 g, 0.406 mmol). The mixture was stirred at rt for 1 hr. The mixture was diluted with sat'd. aq. NaHCO3 and CH2Cl2 and extracted 3× with CH2Cl2. The combined organics were dried (anted. Na2SO4), filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (400 MHz, CDCl3) δ 7.22-7.40 (m, 5H), 4.38 (d, 1H, J=10.4 Hz), 3.96 (d, 1H, J=10.2 Hz), 3.35 (t, 1H, J=9.4 Hz), 2.62-2.85 (m, 2H), 1.15-2.40 (m, 12H), 0.81-0.99 (m, 6H). HRMS (ES) m/z M+H calc'd:331.2380. found: 331.2379.

Workup

  1. additionThe mixture was diluted with sat'd
  2. extractionaq. NaHCO3 and CH2Cl2 and extracted 3× with CH2Cl2
  3. dry with materialThe combined organics were dried (anted. Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8170f1db08b946b89b453a0f18764178
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

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