2-Furancarboxylic acid → HCID 86588453, compound

HRID 229832Notes

Reaction equation

HRID 229832 reaction equation
CN(C)CCCN=C=NCC.[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]([OH:19])=O.[NH2:20][C@@H:21]([CH2:37][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1)[C:22]([NH:24][C@H:25]1[CH2:31][CH2:30][C@@H:29]([CH3:32])[N:28]([CH2:33][CH2:34][CH3:35])[CH2:27][C@@H:26]1[OH:36])=[O:23].CN1CCOCC1.OC1C2N=NNC=2C=CC=1>CN(C=O)C.CCOC(C)=O>[CH:38]1([CH2:37][C@H:21]([NH:20][C:17]([C:13]2[O:12][CH:16]=[CH:15][CH:14]=2)=[O:19])[C:22](=[O:23])[NH:24][C@H:25]2[CH2:31][CH2:30][C@@H:29]([CH3:32])[N:28]([CH2:33][CH2:34][CH3:35])[CH2:27][C@@H:26]2[OH:36])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

8

Reactant 5

HCID 69192-Furancarboxylic acidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 68999700HCID 68999700, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 86588453HCID 86588453, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide (0.10 g, 0.53 mmol) was added to a solution of furan-2-carboxylic acid (0.059 g, 0.53 mmol), (S)-2-Amino-3-cyclohexyl-N-((3S,4S,7R)-3-hydroxy-7-methyl-1-propyl-azepan-4-yl)-propionamide (0.15 g, 0.36 mmol), 4-methylmorpholine (0.14 g, 0.16 ml, 1.44 mmol), hydroxybenztriazole (0.071 g, 0.53 mmol) in DMF (2.0 ml) and was stirred at RT overnight. The reaction mixture was then warmed to RT and was stirred overnight. The reaction mixture was diluted with EtOAc (30 ml), washed with H2O, brine, dried with magnesium sulfate, filtered, concentrated in vacuo by rotary evaporation, and chromatographed (silica gel, 2.5% MeOH/CH2Cl2) to yield the title compound (0.12 g, 76%): Electrospray mass spec: M+H+=434.2.

Workup

  1. temperatureThe reaction mixture was then warmed to RT
  2. stirringwas stirred overnight
  3. washwashed with H2O, brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo by rotary evaporation
  7. customchromatographed (silica gel, 2.5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f6485a9f7b36494b8293aaa789e73f10
Source dataset
uspto-grants-2009_07
Patent number
US07563784B2

Reaction notes

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