Hydrochloric Acid → HCID 54347949, compound

HRID 1489167Notes

Reaction equation

HRID 1489167 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:11]([C@@:13]1([CH2:27][F:28])[CH2:17][C:16](=O)[N:15]([C@@H:19]([CH3:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14]1)=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.S(=O)(=O)(O)O.Cl.[OH-].[Na+]>O1CCCC1>[CH2:3]([N:10]([CH2:11][C@@:13]1([CH2:27][F:28])[CH2:17][CH2:16][N:15]([C@@H:19]([CH3:26])[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:14]1)[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 67715636HCID 67715636, compound

Product 1

HCID 54347949HCID 54347949, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium borohydride (12.2 g) was added to a solution of (R)-N,N-dibenzyl-3-fluoromethyl-1-((S)-α-methylbenzyl)-5-oxopyrrolidine-3-carboxamide (28.6 g) obtained in Preparative Example 10 in tetrahydrofuran (300 ml), and a solution of conc. sulfuric acid (8.6 ml) in tetrahydrofuran (100 ml) was dropwise added at not more than 5° C. over 1 hour. 3N Hydrochloric acid (78 ml) was dropwise added under ice-cooling and the mixture was refluxed for 1 hour with stirring. The reaction mixture was made alkaline by an aqueous solution of sodium hydroxide, and extracted with ethyl acetate, washed with water, dried, concentrated, and purified by silica gel column chromatography to give the object compound as an oil.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was refluxed for 1 hour
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-9f8e4d640435430c9b5e3a26b4296766
Source dataset
uspto-grants-1997_10
Patent number
US05677316

Reaction notes

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