Citric Acid → HCID 72253702, compound

HRID 1429138Notes

Reaction equation

HRID 1429138 reaction equation
[CH3:1][O:2][C:3]1[CH:48]=[CH:47][C:6]([CH2:7][N:8]2[C:26](=[O:27])[N:25]3[CH:21]([CH2:22][CH:23]([O:28][C:29]4[CH:34]=[C:33]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[N:32]=[C:31]([O:41][CH3:42])[N:30]=4)[CH2:24]3)[C:20](=[O:43])[NH:19][C:18]3([C:44](O)=[O:45])[CH:16]([CH2:17]3)[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:5][CH:4]=1.CCN=C=NCCCN(C)C.[CH3:60][C:61]1([S:64]([NH2:67])(=[O:66])=[O:65])[CH2:63][CH2:62]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[CH:48]=[CH:47][C:6]([CH2:7][N:8]2[C:26](=[O:27])[N:25]3[CH:21]([CH2:22][CH:23]([O:28][C:29]4[CH:34]=[C:33]([C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=5)[N:32]=[C:31]([O:41][CH3:42])[N:30]=4)[CH2:24]3)[C:20](=[O:43])[NH:19][C:18]3([C:44]([NH:67][S:64]([C:61]4([CH3:60])[CH2:63][CH2:62]4)(=[O:66])=[O:65])=[O:45])[CH:16]([CH2:17]3)[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:5][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 68591016HCID 68591016, compound

Product 1

HCID 72253702HCID 72253702, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 2d (130 mg, 0.198 mmol) was dissolved in DCM (10 ml). EDAC (46 mg, 0.238 mmol) was added and the reaction mixture was stirred at RT for 2.5 h. Methyl cyclopropanesulfonic amide (30 mg, 0.3218 mmol) and DBU (63 μl, 0.416 mmol) were added and the mixture was stirred at RT over night. 5% Citric acid was added and the organic layer was washed with brine, dried, filtered and evaporated. The material was used directly in the following step without further purification.

Workup

  1. stirringthe mixture was stirred at RT over night
  2. washthe organic layer was washed with brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe material was used directly in the following step without further purification

Sources & evidence

ORD record
ord-37e580e4d9e045329c72608962a531c4
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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