Triphenylphosphine → HCID 86673853, compound

HRID 1527417Notes

Reaction equation

HRID 1527417 reaction equation
[O:1]=[O+][O-].[C:4]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([F:16])[C@@H:13]([O:17][CH2:18][CH:19]=C)[C@H:12]1[C:21](=[O:32])[NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=1[F:31])=[O:10])([CH3:7])([CH3:6])[CH3:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[C:4]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([F:16])[C@@H:13]([O:17][CH2:18][CH:19]=[O:1])[C@H:12]1[C:21](=[O:32])[NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=1[F:31])=[O:10])([CH3:7])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24823Ozone2×HCID 68283865HCID 68283865, compound

Product 1

HCID 86673853HCID 86673853, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ozone was bubbled through a solution of (2S,3S,4S)-3-allyloxy-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-pyrrolidine-1-carboxylic acid tert-butyl ester (59 mg, 0.137 mmol) in CH2Cl2 (20 mL) at −78° C. When the solution turned blue, ozone addition was stopped and nitrogen was passed through the solution until the blue color was discharged. Triphenylphosphine (35.9 mg, 0.137 mmol) was added to the ozonide solution at −78° C. and the reaction mixture was allowed to slowly reach RT. The reaction mixture was concentrated and the material thus obtained used without further purification in the next step. MS (UPLC): 433.4/435.4 [M+H]+, 477.4/579.5 [M+HCOO]−.

Workup

  1. customwas allowed to slowly reach RT
  2. concentrationThe reaction mixture was concentrated
  3. customthe material thus obtained
  4. customused without further purification in the next step

Sources & evidence

ORD record
ord-3c6260c017dd4cfeb1b35178cf337383
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…