Potassium Carbonate → HCID 57751163, compound

HRID 335671Notes

Reaction equation

HRID 335671 reaction equation
[C:1]([C@H:5]([NH:9][NH:10][C:11](=[O:21])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:13]=1[CH3:20])[CH2:6][CH2:7][CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([O:34][CH3:35])[C:32]=1[CH3:33])[C:27](Cl)=[O:28].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[C:1]([C@H:5]([N:9]([C:27](=[O:28])[C:26]1[CH:30]=[C:31]([O:34][CH3:35])[C:32]([CH3:33])=[C:24]([O:23][CH3:22])[CH:25]=1)[NH:10][C:11](=[O:21])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:13]=1[CH3:20])[CH2:6][CH2:7][CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 226200193,5-Dimethoxy-4-methylbenzoyl chlorideHCID 57751158HCID 57751158, compound

Product 1

HCID 57751163HCID 57751163, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-3-methoxy-2-methyl-benzoic acid N′-(1-tert-butyl-butyl)-hydrazide (100 mg, 0.34 mmol) and 3,5-dimethoxy-4-methyl-benzoyl chloride (90 mg, 0.41 mmol) were dissolved in 1 mL methylene chloride. 1.5 eq. of ca. 25% K2CO3 was added, and the reaction mixture was stirred at room temperature and monitored by TLC. Upon completion, the phases were separated, adding additional CH2Cl2 and/or water as needed to aid manipulation. The CH2Cl2 phase was dried over MgSO4 or Na2SO4, and solvent was removed in vacuo to provide an oily solid. This was triturated with 1:1 hexane:ether and allowed to dry in air to yield (R)-3,5-Dimethoxy-4-methyl-benzoic acid N-(1-tert-butyl-butyl)-N′-(3-methoxy-2-methyl-benzoyl)-hydrazide. Rf=0.29 (2:1 hexanes:ethyl acetate); 1H NMR (400 MHz, CDCl3) δ 7.1 (t, 1H), 7.0 (s, NH 1H), 6.9 (d, 1H), 6.7 (s, 2H), 6.3 (d, 1H), 4.78 (m, 1H), 3.95 (s, 3H), 3.85 (2s, 6H), 2.2 (s, 3H), 2.05 (m, 1H), 1.95 (s, 3H), 1.8 (m, 1H), 1.6 (m, 2H), 1.2+1.1+1.05 (3s, 9H), 1.05 (m, 3H); HRMS (ESI) m/z calcd for C27H39N2O5 [M+H]+ 471.2859. found 471.2850, calcd for C27H38NaN2O5 [M+Na]+ 493.2670. found 493.2678.

Workup

  1. customUpon completion, the phases were separated
  2. additionadding additional CH2Cl2 and/or water
  3. dry with materialThe CH2Cl2 phase was dried over MgSO4 or Na2SO4, and solvent
  4. customwas removed in vacuo
  5. customto provide an oily solid
  6. customThis was triturated with 1:1 hexane
  7. customto dry in air

Sources & evidence

ORD record
ord-d7deb7bfdbd84ae886d2b699b23b949b
Source dataset
uspto-grants-2014_11
Patent number
US08884060B2

Reaction notes

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