Triphenylphosphine → HCID 22508860, compound

HRID 1163059Notes

Reaction equation

HRID 1163059 reaction equation
[F:1][C:2]1[C:10]([O:11][C:12]2[C:17]3=[C:18]([CH3:27])[C:19]([O:21][CH2:22][CH2:23][CH2:24][S:25][CH3:26])=[CH:20][N:16]3[N:15]=[CH:14][N:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:28])[NH:6]2.C1C=C(Cl)C=C(C(OO)=[O:37])C=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[F:1][C:2]1[C:10]([O:11][C:12]2[C:17]3=[C:18]([CH3:27])[C:19]([O:21][CH2:22][CH2:23][CH2:24][S:25]([CH3:26])=[O:37])=[CH:20][N:16]3[N:15]=[CH:14][N:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:28])[NH:6]2

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 70297m-Chloroperbenzoic acidHCID 22508864HCID 22508864, compound

Product 1

HCID 22508860HCID 22508860, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Example 29 (25 mg, 0.0625 mmol) in dichloromethane at 0° C. was added m-CPBA (77%, 14 mg, 0.0625 mmol). After stirring the mixture at 0° C. for 30 min, triphenylphosphine (5 mg, 0.019 mmol) was added. After stirring at 0° C. for additional 30 min, the reaction mixture was concentrated in vacuo. The crude material was purified by preparative HPLC to afford the title compound (11 mg, 42% yield) as a white solid. MS: (M+H)+=417.

Workup

  1. stirringAfter stirring at 0° C. for additional 30 min
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-d6bd6a1f425e432c9a04502ccd230390
Source dataset
uspto-grants-2010_10
Patent number
US07820814B2

Reaction notes

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