Allyl iodide → HCID 68283865, compound

HRID 1527416Notes

Reaction equation

HRID 1527416 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:14][C@H:13]([F:15])[C@@H:12]([OH:16])[C@H:11]1[C:17](=[O:28])[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[F:27])=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH2:29](I)[CH:30]=[CH2:31]>CN(C=O)C>[C:3]([O:7][C:8]([N:10]1[CH2:14][C@H:13]([F:15])[C@@H:12]([O:16][CH2:31][CH:30]=[CH2:29])[C@H:11]1[C:17](=[O:28])[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[F:27])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 11166Allyl iodideHCID 24758Sodium hydrideHCID 68284010HCID 68284010, compound

Product 1

HCID 68283865HCID 68283865, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of NaH (60% in mineral oil, 8.6 mg, 0.215 mmol) in DMF (5 mL) cooled with an ice-bath and under argon was added (2S,3S,4S)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (70 mg, 0.179 mmol). The reaction mixture was stirred for 20 min before addition of allyl iodide (0.025 mL, 0.269 mmol) at 0° C. The reaction mixture was stirred for 30 min then quenched by addition of water and extracted with EtOAc (×2). The organic extracts were combined, washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 3:2). MS (UPLC): 431.4/433.1 [M+H]+, 475.5/577.5 [M+HCOO]−; tR (HPLC conditions f): 2.29 min.

Workup

  1. customthen quenched by addition of water
  2. extractionextracted with EtOAc (×2)
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 3:2)
  8. custom2.29 min.

Sources & evidence

ORD record
ord-f9cce5e76f0c4aed8c88de34fef0a70d
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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