Dimethylformamide → HCID 67009874, compound

HRID 1630282Notes

Reaction equation

HRID 1630282 reaction equation
N1CCOCC1.[N:7]1([CH2:12][C:13]([N:15]2[C@H:19]([C:20](=[O:36])[NH:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)=[CH:24][CH:23]=3)[CH2:18][C@H:17]([NH:37]C(=O)OCC3C4C=CC=CC=4C4C3=CC=CC=4)[CH2:16]2)=[O:14])[CH:11]=[N:10][CH:9]=[N:8]1.CN(C=O)C>O>[N:7]1([CH2:12][C:13]([N:15]2[CH2:16][C@@H:17]([NH2:37])[CH2:18][C@H:19]2[C:20]([NH:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)=[CH:26][CH:27]=2)=[O:36])=[O:14])[CH:11]=[N:10][CH:9]=[N:8]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8083MorpholineHCID 86659491(9H-fluoren-9-yl)methyl (3S,5S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamate

Product 1

HCID 67009874HCID 67009874, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Step (a) Morpholine (10 mL) was added to a flask charged with the (9H-fluoren-9-yl)methyl (3S,5S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamate (0.859 g, 1.33 mmol), prepared as in prepared as in Example 1, and DMF (10 mL). The reaction mixture was stirred at ambient temperature for 30 minutes and then diluted with deionized water (20 mL). The dilution was extracted with ethyl acetate (60 mL) and the extract was washed with brine (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give (2S,4S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-amino-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (0.465 g, 1.10 mmol), which was carried forward without further purification.

Workup

  1. extractionThe dilution was extracted with ethyl acetate (60 mL)
  2. washthe extract was washed with brine (30 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2415469f0d834cafab40128fa8cf840a
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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