Citric Acid → HCID 66922143, compound

HRID 2039872Notes

Reaction equation

HRID 2039872 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[N:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:17]=2[O:31][C:32]2[C:37]([CH3:38])=[CH:36][CH:35]=[CH:34][C:33]=2[CH3:39])=[O:15])[CH2:10][CH:9]1[CH2:40][C:41]([O:43]C)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:45][NH2:46].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[N:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:17]=2[O:31][C:32]2[C:33]([CH3:39])=[CH:34][CH:35]=[CH:36][C:37]=2[CH3:38])=[O:15])[CH2:10][CH:9]1[CH2:40][C:41](=[O:43])[NH:46][CH3:45])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 311Citric AcidHCID 6329MethylamineHCID 66922257HCID 66922257, compound

Product 1

HCID 66922143HCID 66922143, compoundYield 32.2%

Conditions

Temperature
40 °C

Procedure

A solution of the crude compound of example 58, step 2, (140 mg, 234 μmol) in MOH (1 ml) was mixed with a 2 M methanolic solution of methylamine (2.60 ml, 5.19 mmol). The reaction mixture was stirred at 40° C. for 7 days. After cooling to room temperature, the mixture was neutralized with an aqueous solution of citric acid and extracted with EA. The combined organic phases were dried over sodium sulfate and evaporated. 45 mg of crude title compound were obtained.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EA
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-d8d5542763a64eae8fc588d2c024ea97
Source dataset
uspto-grants-2013_11
Patent number
US08580813B2

Reaction notes

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