Citric Acid → HCID 75277258, compound

HRID 1429165Notes

Reaction equation

HRID 1429165 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH:10]2[CH2:27][CH:26]3[CH:12]([C:13](=[O:33])[N:14]([CH3:32])[CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH:20][CH:21]4[C:23]([C:29](O)=[O:30])([NH:24][C:25]3=[O:28])[CH2:22]4)[CH2:11]2)[CH:6]=[C:5]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:4]=1.CCN=C=NCCCN(C)C.[CH3:51][C:52]1([S:55]([NH2:58])(=[O:57])=[O:56])[CH2:54][CH2:53]1.C1CCN2C(=NCCC2)CC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH:10]2[CH2:27][CH:26]3[CH:12]([C:13](=[O:33])[N:14]([CH3:32])[CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH:20][CH:21]4[C:23]([C:29]([NH:58][S:55]([C:52]5([CH3:51])[CH2:54][CH2:53]5)(=[O:57])=[O:56])=[O:30])([NH:24][C:25]3=[O:28])[CH2:22]4)[CH2:11]2)[CH:6]=[C:5]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:4]=1

Participants

7

Reactant 5

HCID 311Citric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 218898141-Methylcyclopropane-1-sulfonamideHCID 68591013HCID 68591013, compound

Product 1

HCID 75277258HCID 75277258, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the acid 13e (250 mg, 0.46 mmol) and EDAC (150 mg, 0.6 mmol) in dry DCM (4 ml) was stirred overnight at room temperature. Methylcyclopropane sulphonamide (78 mg, 0.58 mmol) and DBU (182 mg, 1.2 mmol) were added and the mixture was stirred for additional 6 hours at room temperature. 5% Citric acid was added and the mixture was extracted with ethyl acetate. The organic phase was washed two times with 5% citric acid and water, dried with sodium sulphate and evaporated under reduced pressure. Purification by column chromatography on silica gel eluted with diethyl ether-ethyl acetate gave the pure title compound, (130 mg, 44%), (M+H)+652.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phase was washed two times with 5% citric acid and water
  3. dry with materialdried with sodium sulphate
  4. customevaporated under reduced pressure
  5. customPurification by column chromatography on silica gel
  6. washeluted with diethyl ether-ethyl acetate

Sources & evidence

ORD record
ord-a43f4a46007d4158babb5449dd43dad5
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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