Triphenylphosphine → HCID 20482757, compound

HRID 1389370Notes

Reaction equation

HRID 1389370 reaction equation
[Cl:1]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:28]1([NH:34][CH:35]([CH:39](O)[CH3:40])[C:36]([O-:38])=[O:37])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1>[C:28]1([NH:34][CH:35]([CH:39]([Cl:1])[CH3:40])[C:36]([OH:38])=[O:37])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 20482783HCID 20482783, compound

Product 1

HCID 20482757HCID 20482757, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of N-chlorosuccinimide (1.24 g) and dry THF (60 ml), stirring at RT, is slowly added triphenylphosphine (2.43 g) in 50 ml of THF. Then the m-phenoxybenzyl ester of 2-phenylamino-3-hydroxybutanoate (3.5 g) in 30 ml of THF is added slowly. The reaction mixture is stirred overnight. The reaction is then concentrated under reduced pressure. The residue (oil) is taken up in ether, washed with water, dried over magnesium sulfate and evaporated to yield the m-phenoxybenzyl ester of 2-phenylamino-3-chloro-butanoic acid, MS m/e 395 (M+).

Workup

  1. concentrationThe reaction is then concentrated under reduced pressure
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-bd08685e68be4209bfedad0fadc4b0bb
Source dataset
uspto-grants-1981_01
Patent number
US04243819

Reaction notes

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