Citric Acid → HCID 74341329, compound

HRID 1429150Notes

Reaction equation

HRID 1429150 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:6]=[C:5]([O:15][CH:16]2[CH2:33][CH:32]3[CH:18]([C:19](=[O:39])[N:20]([CH3:38])[CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH:26][CH:27]4[C:29]([C:35](O)=[O:36])([NH:30][C:31]3=[O:34])[CH2:28]4)[CH2:17]2)[CH: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]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:6]=[C:5]([O:15][CH:16]2[CH2:33][CH:32]3[CH:18]([C:19](=[O:39])[N:20]([CH3:38])[CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH:26][CH:27]4[C:29]([C:35]([NH:58][S:55]([C:52]5([CH3:51])[CH2:54][CH2:53]5)(=[O:57])=[O:56])=[O:36])([NH:30][C:31]3=[O:34])[CH2:28]4)[CH2:17]2)[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 68591104HCID 68591104, compound

Product 1

HCID 74341329HCID 74341329, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 7e (100 mg, 0.187 mmol) was dissolved in DCM (5 ml), and EDAC (43 mg, 0.224 mmol) was added. The reaction mixture was stirred at RT for 1 h. Methylcyclopropanesulfonic amide (28 mg, 0.206 mmol) and DBU (59 μl, 0.393 mmol) were added and the reaction mixture was stirred at RT over night. Citric acid was added and the organic layer was separated, washed with brine, dried, filtered and evaporated. Purification of the residue by preparative HPLC provided the pure title compound (110 mg, 90%), MS (M+H)+652.

Workup

  1. stirringthe reaction mixture was stirred at RT over night
  2. customthe organic layer was separated
  3. washwashed with brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customPurification of the residue by preparative HPLC

Sources & evidence

ORD record
ord-7f5403e50e774b088f02071accffafad
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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