Citric Acid → HCID 72253701, compound

HRID 1429128Notes

Reaction equation

HRID 1429128 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]([OH:46])=O)[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.[CH:60]1([S:63]([NH2:66])(=[O:65])=[O:64])[CH2:62][CH2:61]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: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]([NH:66][S:63]([CH:60]4[CH2:62][CH2:61]4)(=[O:65])=[O:64])=[O:46])[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 15765418CyclopropanesulfonamideHCID 68591016HCID 68591016, compound

Product 1

HCID 72253701HCID 72253701, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 2d (200 mg, 0.305 mmol) was dissolved in DCM (10 ml). EDAC (70 mg, 0.366 mmol) was added and the reaction mixture was stirred at RT for 30 min. Cyclopropanesulfonic amide (41 mg, 0.336 mmol) and DBU (96 μl, 0.641 mmol) were added and the reaction was stirred at RT for 72 h. 5% Citric acid was added and the organic layer was separated and washed with brine, dried, filtered and evaporated. This material was used directly in the following step without further purification.

Workup

  1. stirringthe reaction was stirred at RT for 72 h
  2. customthe organic layer was separated
  3. washwashed with brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThis material was used directly in the following step without further purification

Sources & evidence

ORD record
ord-c74b6de53de44ac8abbf2153b4f55526
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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