Water → HCID 57751156, compound

HRID 658566Notes

Reaction equation

HRID 658566 reaction equation
[CH:1]1([C@H:7]([NH:11][NH:12][C:13](=[O:23])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[C:15]=2[CH3:22])[CH2:8][CH:9]=[CH2:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].O.[CH3:31][C:32]1[CH:33]=[C:34]([CH:38]=[C:39]([CH3:41])[CH:40]=1)[C:35](Cl)=[O:36]>C(Cl)Cl>[CH:1]1([C@H:7]([N:11]([C:35](=[O:36])[C:34]2[CH:38]=[C:39]([CH3:41])[CH:40]=[C:32]([CH3:31])[CH:33]=2)[NH:12][C:13](=[O:23])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[C:15]=2[CH3:22])[CH2:8][CH:9]=[CH2:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 810883,5-Dimethylbenzoyl ChlorideHCID 57751170HCID 57751170, compound

Product 1

HCID 57751156HCID 57751156, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (R)-3-methoxy-2-methyl-benzoic acid N′-(1-cyclohexyl-but-3-enyl)-hydrazide (1.3 g, 4.11 mmol) in CH2Cl2 (5 mL), was added K2CO3 (2.27 g, 16.44 mmol), H2O (5 mL), and finally 3,5-dimethylbenzoyl chloride (727 mg, 4.31 mmol). The reaction was stirred at room temperature for 24 h. Additional CH2Cl2 and H2O were added to aid manipulation, the CH2Cl2 layer was separated, and the aqueous layer was extracted with CH2Cl2. The CH2Cl2 solutions were combined and dried over anhydrous Na2SO4. The solvent was evaporated in vacuo and the residue was purified by flash chromatography to provide (R)-3,5-dimethyl-benzoic acid N-(1-cyclohexyl-but-3-enyl)-N′-(3-methoxy-2-methyl-benzoyl)-hydrazide as a white solid (1.45 g, 78% yield). Rf=0.21 (3:1 EtOAc:n-Hexane); 1H NMR (400 MHz, DMSO-d6) δ 10.47+10.39 (2 s, 1H), 7.20-7.01 (m, 5H), 6.37 (d, J=7.2 Hz, 1H), 6.22-5.89 (m, 1H), 5.18 (dd, 1H), 5.02 (dd, 1H), 4.46 (m, 1H), 3.79 (s, 3H), 2.44-2.34 (m, 2H), 2.29 (s, 3H), 2.02-1.53 (m, 8H), 1.26-1.02 (m, 3H); HRMS (ESI) m/z calcd for C28H37N2O3 [M+H]+ 449.2804, found 449.2793, calcd for C28H36N2NaO3 [M+Na]+ 471.2624, found 471.2615.

Workup

  1. customthe CH2Cl2 layer was separated
  2. extractionthe aqueous layer was extracted with CH2Cl2
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-25f441f932fa4d5cb3afe068a614a145
Source dataset
uspto-grants-2011_12
Patent number
US08076517B2

Reaction notes

Loading…