Azobisisobutyronitrile → HCID 68283984, compound

HRID 1527401Notes

Reaction equation

HRID 1527401 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@:11]([F:25])([CH2:13]OC(OC2C=CC(F)=CC=2)=S)[CH2:10][C@H:9]1[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(N=NC(C#N)(C)C)(C#N)C.C[Si]([SiH]([Si](C)(C)C)[Si](C)(C)C)(C)C>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@:11]([F:25])([CH3:13])[CH2:10][C@H:9]1[C:26]([O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:27])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 123134Tris(trimethylsilyl)silaneHCID 86673846HCID 86673846, compound

Product 1

HCID 68283984HCID 68283984, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (2S,4R)-4-fluoro-4-(4-fluoro-phenoxythiocarbonyloxymethyl)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (290 mg, 0.57 mmol) in dioxane (5 mL) were added VAZO (69 mg, 0.28 mmol) and tris(trimethylsilyl)silane (0.24 mL, 0.77 mmol). The reaction mixture was refluxed for 30 min then was stirred for 16 h at RT and concentrated. Purification by flash column chromatography on silica gel (c-hexane/EtOAc 4:1). MS (UPLC/MS): 338 [M+H]+; tR (HPLC conditions f): 2.38 min.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 min
  2. concentrationconcentrated
  3. customPurification by flash column chromatography on silica gel (c-hexane/EtOAc 4:1)
  4. custom2.38 min.

Sources & evidence

ORD record
ord-b0e86867ee6f44f98e77797c7775ec48
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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