Triphenylphosphine → HCID 58745567, compound

HRID 723488Notes

Reaction equation

HRID 723488 reaction equation
[N:1]([C@@H:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][C@H:5]1[NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.O>[NH2:1][C@@H:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][C@H:5]1[NH:20][S:21]([CH3:24])(=[O:23])=[O:22]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 58745560HCID 58745560, compound

Product 1

HCID 58745567HCID 58745567, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred mixture of Compound 264B (530 mg, 1.50 mmoL) in 6 mL of THF and 1 mL of water was added Ph3P (900 mg, 3.43 mmoL). The reaction mixture was heated at 70° C. for 15 h and cooled to room temperature. This mixture was concentrated in vacuo, diluted with 15 mL of 2N HCl solution, and then washed with CHCl3 (3×20 mL). The aqueous was basified to pH 12 by the addition of 50% NaOH solution, saturated with NaCl, and then extracted with EtOAc (3×25 mL). The combined EtOAc extracts were washed with brine (15 mL), dried (MgSO4), filtered and concentrated in vacuo to give 490 mg (yield: 100%) of Compound 264C. It had an analytical HPLC retention time=1.67 min. (Phenomenox S5 C18-HC 4.6×50 mm column, 10–90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 ml/min, monitoring at 220 nm) and a LC/MS M++1=328.

Workup

  1. temperaturecooled to room temperature
  2. concentrationThis mixture was concentrated in vacuo
  3. additiondiluted with 15 mL of 2N HCl solution
  4. washwashed with CHCl3 (3×20 mL)
  5. additionThe aqueous was basified to pH 12 by the addition of 50% NaOH solution, saturated with NaCl
  6. extractionextracted with EtOAc (3×25 mL)
  7. washThe combined EtOAc extracts were washed with brine (15 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e5c675879fe64557a2e29b6acd67263d
Source dataset
uspto-grants-2006_11
Patent number
US07141571B2

Reaction notes

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