Citric Acid → HCID 75277248, compound

HRID 1429124Notes

Reaction equation

HRID 1429124 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH:10]2[CH2:27][CH:26]3[N: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[N: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: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 15765418CyclopropanesulfonamideHCID 72253703HCID 72253703, compound

Product 1

HCID 75277248HCID 75277248, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 1i (78 mg, 0.146 mmol) and EDAC (34 mg, 0.175 mmol) were dissolved in DCM (3 ml). The reaction mixture was stirred at room temperature for 1 h (LC-MS indicated presence of the intermediate). Cyclopropane sulphonic amide (20 mg, 0.161 mmol) and DBU (46 μl, 0.307 mmol) were added and the reaction mixture was stirred at RT for 3.5 h. Citric acid (5%) was added and the organic layer was separated and washed with brine, dried (MgSO4), filtered and evaporated. The residue was purified by preparative HPLC which gave the pure title compound (50 mg, 54%), (M+H)+639).

Workup

  1. stirringthe reaction mixture was stirred at RT for 3.5 h
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by preparative HPLC which

Sources & evidence

ORD record
ord-81fcc464a21644e799c2a1f7d4875eb7
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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