Citric Acid → HCID 131732365, compound

HRID 1429164Notes

Reaction equation

HRID 1429164 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]([OH:31])=O)([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.[CH:51]1([S:54]([NH2:57])(=[O:56])=[O:55])[CH2:53][CH2:52]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:57][S:54]([CH:51]5[CH2:53][CH2:52]5)(=[O:56])=[O:55])=[O:31])([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

Participants

7

Reactant 5

HCID 311Citric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15765418CyclopropanesulfonamideHCID 68591013HCID 68591013, compound

Product 1

HCID 131732365HCID 131732365, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the acid 13e (150 mg, 0.28 mmol) and EDAC (65 mg, 0.34 mmol) in dry DCM (3 ml) was stirred overnight. Cyclopropane sulphonamide (72.7 mg, 0.6 mmol) and DBU (120 mg, 0.8 mmol) was added and the mixture was stirred overnight 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 HPLC gave the title compound, (100 mg, 56%), (M+H)+638

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 HPLC

Sources & evidence

ORD record
ord-8630a4e1261940b9b88146b68cd10c03
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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