Citric Acid → HCID 73436958, compound

HRID 1443484Notes

Reaction equation

HRID 1443484 reaction equation
[CH3:1][O:2][C:3]1[C:12]([CH3:13])=[C:11]2[C:6]([C:7]([O:22][CH:23]3[CH2:40][CH:39]4[N:25]([C:26](=[O:46])[N:27]([CH3:45])[CH2:28][CH2:29][CH2:30][CH2:31][CH:32]=[CH:33][CH:34]5[C:36]([C:42](O)=[O:43])([NH:37][C:38]4=[O:41])[CH2:35]5)[CH2:24]3)=[N:8][C:9]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[N:10]2)=[CH:5][CH:4]=1.CCN=C=NCCCN(C)C.[CH3:58][C:59]1([S:62]([NH2:65])(=[O:64])=[O:63])[CH2:61][CH2:60]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[C:12]([CH3:13])=[C:11]2[C:6]([C:7]([O:22][CH:23]3[CH2:40][CH:39]4[N:25]([C:26](=[O:46])[N:27]([CH3:45])[CH2:28][CH2:29][CH2:30][CH2:31][CH:32]=[CH:33][CH:34]5[C:36]([C:42]([NH:65][S:62]([C:59]6([CH3:58])[CH2:61][CH2:60]6)(=[O:64])=[O:63])=[O:43])([NH:37][C:38]4=[O:41])[CH2:35]5)[CH2:24]3)=[N:8][C:9]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)=[N:10]2)=[CH:5][CH: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 68408720HCID 68408720, compound

Product 1

HCID 73436958HCID 73436958, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The acid (130) (35 mg, 0.056 mmol) was dissolved in DCM (2 ml). EDAC (13 mg, 0.067 mmol) was added and the mixture was stirred at room temperature over night. Methylcyclopropanesulfonic acid amide (8.2 mg, 0.061 mmol) and DBU (18 μl, 0.117 mmol) was added and the reaction mixture was stirred at room temperature over night. 5% Citric acid was added to the reaction mixture, and the mixture was extracted with brine, dried over Na2SO4 and purified by HPLC to give the title compound (9 mg, 22%). MS (M+H)=747.

Workup

  1. stirringthe reaction mixture was stirred at room temperature over night
  2. extractionthe mixture was extracted with brine
  3. dry with materialdried over Na2SO4
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-dd8d7a3eca884cf29b14632b350ab813
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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