Triphenylphosphine → HCID 59710981, compound

HRID 2376806Notes

Reaction equation

HRID 2376806 reaction equation
[N:1]([CH2:4][C@@H:5]([NH:12][C:13]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[C:20]([NH:25][C:26]([C:28]1[C:29]([C:34]3[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=3)=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:27])[CH:19]=[CH:18]2)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1>[NH2:1][CH2:4][C@@H:5]([NH:12][C:13]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[C:20]([NH:25][C:26]([C:28]1[C:29]([C:34]3[CH:35]=[CH:36][C:37]([C:40]([F:43])([F:41])[F:42])=[CH:38][CH:39]=3)=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:27])[CH:19]=[CH:18]2)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 59710974HCID 59710974, compound

Product 1

HCID 59710981HCID 59710981, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

(S)-2-[(4′-Trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-6-carboxylic acid (2-azido-1-phenyl-ethyl)amide (M, 0.722 mg, 1.22 mM) was dissolved in dioxane (10 mL). Triphenyl phosphine (0.35 g, 1.34 mM) was added and the mixture was stirred at 50° C. for 4 h. The mixture was removed from the heat and treated with an aqueous solution of NaOH (1N, 5 mL). The resulting mixture was stirred at room temperature for 2 h. The mixture was treated with 1N HCl (10 mL) and stirred for 12 h. The precipitate was collected by filtration and washed with ether. The solid was dried under high vacuum to provide (S)-2-[(4′-trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-6-carboxylic acid (2-amino-1-phenyl-ethyl)-amide. ESMS (m+1), 555; calc. Mw, 554

Workup

  1. customThe mixture was removed from the
  2. temperatureheat
  3. additiontreated with an aqueous solution of NaOH (1N, 5 mL)
  4. stirringThe resulting mixture was stirred at room temperature for 2 h
  5. additionThe mixture was treated with 1N HCl (10 mL)
  6. stirringstirred for 12 h
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with ether
  9. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-25dc56313e484bf682f008d4daf7067a
Source dataset
uspto-grants-2008_12
Patent number
US07468378B2

Reaction notes

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