Hydrochloric Acid → HCID 67490993, compound

HRID 1917302Notes

Reaction equation

HRID 1917302 reaction equation
C([N-]C(C)C)(C)C.[Li+].[C:9]([O:13][C:14]([C@@:16]1([CH2:30][CH2:31][O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[CH2:20][C:19](=[O:21])[N:18]([C@@H:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH3:23])[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:50])(=O)=O)=CC=1.[Cl-].[NH4+].Cl>O1CCCC1.C(OCC)(=O)C>[C:9]([O:13][C:14]([C@@:16]1([CH2:30][CH2:31][O:32][Si:33]([C:36]([CH3:38])([CH3:37])[CH3:39])([CH3:35])[CH3:34])[CH:20]([F:50])[C:19](=[O:21])[N:18]([C@@H:22]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH3:23])[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 588007N-FluorobenzenesulfonimideHCID 2724682Lithium diisopropylamideHCID 67490763(3S)-3-[2-(tert-Butyldimethylsilyloxy)ethyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 67490993HCID 67490993, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A 1.8 M solution of lithium diisopropylamide in tetrahydrofuran (4.10 mL) was added dropwise to a solution of (3S)-3-[2-(tert-butyldimethylsilyloxy)ethyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester in tetrahydrofuran in a nitrogen atmosphere at −73° C. over 10 minutes. After stirring at the same temperature for 15 minutes, a solution of N-fluorobenzenesulfonimide (2.63 g, 8.33 mmol) in tetrahydrofuran (18 mL) was added dropwise over 15 minutes. After stirring at the same temperature for 30 minutes, a saturated ammonium chloride solution (20 mL) was added, and the mixture was heated to 0° C. The reaction solution was poured into a mixture of ethyl acetate (100 mL) and 1 mol/mL hydrochloric acid (50 mL), followed by extraction with ethyl acetate (200 mL). The organic layer was sequentially washed with a saturated sodium bicarbonate solution (50 mL) and brine (50 mL×2) and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. Dichloromethane was added to the resulting residue to prepare a slurry, and the solid was removed by filtration. The filtrate was concentrated, and the resulting solid was removed by filtration. The filtrate was further concentrated to give 3.44 g of the crude title compound as a pale yellow oil. The resulting crude was used for the next reaction without further purification.

Workup

  1. stirringAfter stirring at the same temperature for 30 minutes
  2. extractionfollowed by extraction with ethyl acetate (200 mL)
  3. washThe organic layer was sequentially washed with a saturated sodium bicarbonate solution (50 mL) and brine (50 mL×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. additionDichloromethane was added to the resulting residue
  8. customto prepare a slurry
  9. customthe solid was removed by filtration
  10. concentrationThe filtrate was concentrated
  11. customthe resulting solid was removed by filtration
  12. concentrationThe filtrate was further concentrated

Sources & evidence

ORD record
ord-909fbacf37694f7ca11e14c06a6fb991
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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