Citric Acid → HCID 68591496, compound

HRID 1429151Notes

Reaction equation

HRID 1429151 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]([OH:37])=O)([NH:30][C:31]3=[O:34])[CH2:28]4)[CH2:17]2)[CH:4]=1.CCN=C=NCCCN(C)C.[C:51]1([S:57]([NH2:60])(=[O:59])=[O:58])[CH:56]=[CH:55][CH:54]=[CH:53][CH: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]([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]([NH:60][S:57]([C:51]5[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=5)(=[O:59])=[O:58])=[O:37])([NH:30][C:31]3=[O:34])[CH2:28]4)[CH2:17]2)[CH:4]=1

Participants

7

Reactant 5

HCID 311Citric AcidHCID 7370BenzenesulfonamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68591104HCID 68591104, compound

Product 1

HCID 68591496HCID 68591496, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 7e (60 mg, 0.112 mmol) was dissolved in DCM (5 ml). EDAC (26 mg, 0.135 mmol) was added and the reaction mixture was stirred at RT over night. benzensulfonamide (19 mg, 0.123 mmol) and DBU (35 μl, 0.235 mmol) were added and the reaction mixture was stirred at RT for 2 h. Citric acid (5%) was added, the organic layer was separated, washed with brine, dried, filtered and evaporated. The residue was purified by preparative HPLC which gave the pure title compound. (36 mg, 48%), MS (M+H)+674.

Workup

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

Sources & evidence

ORD record
ord-130a3da3aba04ea7b94c9d1f2d0d00b3
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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