Triphenylphosphine → HCID 11419738, compound

HRID 602338Notes

Reaction equation

HRID 602338 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]2[CH2:15][C@@H:14]([N:16]=[N+]=[N-])[CH2:13][C@@H:12]2[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][C:29]3=[O:34])=[CH:24][CH:23]=2)=[O:20])=[O:10])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]2[CH2:15][C@@H:14]([NH2:16])[CH2:13][C@@H:12]2[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][C:29]3=[O:34])=[CH:24][CH:23]=2)=[O:20])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 11237058HCID 11237058, compound

Product 1

HCID 11419738HCID 11419738, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

9.4 A solution of 25 mg (0.052 mmol) of “A9” and 20.46 mg (0.08 mmol) of triphenylphosphine in a mixture of 0.5 ml of tetrahydrofuran and 0.5 ml of water is stirred at room temperature for 12 hours. After the precipitated triphenylphosphine oxide has been filtered off, the filtrate is evaporated to dryness, and the residue is purified by preparative HPLC (acetonitrile/water/0.1% trifluoroacetic acid), giving 12 mg (40%) of 1-N-[(4-chlorophenyl)]-2-N-{[4-(3-oxomorpholin-4-yl)phenyl]}-(2R,4S)-4-aminopyrrolidine-1,2-dicarboxamide (“10”) as colourless crystals, ESI 458.

Workup

  1. filtrationAfter the precipitated triphenylphosphine oxide has been filtered off
  2. customthe filtrate is evaporated to dryness
  3. customthe residue is purified by preparative HPLC (acetonitrile/water/0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-6a4da322a3b44269bec73e7ca1310326
Source dataset
uspto-grants-2011_03
Patent number
US07906516B2

Reaction notes

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