Citric Acid → HCID 75277252, compound

HRID 1429140Notes

Reaction equation

HRID 1429140 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([O:11][CH3:12])[N:8]=[C:7]([O:13][CH:14]2[CH2:31][CH:30]3[CH:16]([C:17](=[O:37])[N:18]([CH3:36])[CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH:24][CH:25]4[C:27]([C:33](O)=[O:34])([NH:28][C:29]3=[O:32])[CH2:26]4)[CH2:15]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.[CH3:49][C:50]1([S:53]([NH2:56])(=[O:55])=[O:54])[CH2:52][CH2:51]1.C1CCN2C(=NCCC2)CC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[C:1]([C:5]1[N:10]=[C:9]([O:11][CH3:12])[N:8]=[C:7]([O:13][CH:14]2[CH2:31][CH:30]3[CH:16]([C:17](=[O:37])[N:18]([CH3:36])[CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH:24][CH:25]4[C:27]([C:33]([NH:56][S:53]([C:50]5([CH3:49])[CH2:52][CH2:51]5)(=[O:55])=[O:54])=[O:34])([NH:28][C:29]3=[O:32])[CH2:26]4)[CH2:15]2)[CH:6]=1)([CH3:3])([CH3:4])[CH3:2]

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 68591633HCID 68591633, compound

Product 1

HCID 75277252HCID 75277252, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 3j (120 mg, 0.233 mmol) was dissolved in DCM (10 ml). EDAC (54 mg, 0.28 mmol) was added and the reaction mixture was stirred at RT for 2.5 h. Methyl cyclopropanesulfonic amide (35 mg, 0.256 mmol) and DBU (73 μl, 0.489 mmol) were added and the reaction mixture was stirred at RT over night. 5% Citric acid was added and the organic layer was separated and washed with brine, dried, filtered and evaporated. The residue was purified by preparative HPLC which gave the pure title compound (10.2 mg, 21%), MS (M+H)+632.

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. customThe residue was purified by preparative HPLC which

Sources & evidence

ORD record
ord-028b381c24414e1ba75093990bcc7f5a
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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