Triphenylphosphine → HCID 59710981, compound

HRID 746991Notes

Reaction equation

HRID 746991 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 1 N 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 1 N 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-a9d72475d4254b34bdb6c4ee5b9c38db
Source dataset
uspto-grants-2008_07
Patent number
US07393958B2

Reaction notes

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