Triphenylphosphine → HCID 86627897, compound

HRID 1669417Notes

Reaction equation

HRID 1669417 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:35]([O:37][CH3:38])=[O:36])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][C:24]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)=[CH:25][C:19]=2[O:18][CH2:17][C@@H:16](O)[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(C(C)C)C(C)C.C1C=CC(P([N:81]=[N+:82]=[N-:83])(C2C=CC=CC=2)=O)=CC=1>C1COCC1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>[N:81]([C@@H:16]1[CH2:15][N:14]2[C:13]3[CH:12]=[C:11]([C:35]([O:37][CH3:38])=[O:36])[CH:10]=[CH:9][C:8]=3[C:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[C:21]2[C:20]2[CH:22]=[CH:23][C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)=[CH:25][C:19]=2[O:18][CH2:17]1)=[N+:82]=[N-:83]

Participants

7

Reactant 4

HCID 11776Triphenylphosphine2×HCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azide2×HCID 67343119HCID 67343119, compound

Product 1

HCID 86627897HCID 86627897, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent5×HCID 5363146Diisopropyl azodicarboxylateSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyl (7S)-14-cyclohexyl-7-hydroxy-3-(pyridin-2-ylmethoxy)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate was dissolved in THF (60 mM) and PPh3 (1.2 eq) was added. The solution was cooled to 0° C. and treated with DIPEA (1 eq), followed by slow addition of DIAD (1.2 eq). The mixture was left stirring at this temperature for 5 min, then a solution of DPPA in THF (1.2 eq) was added dropwise. After complete addition the mixture was stirred at 0° C. for further 30 min, then stirring was continued at RT. Since no reaction was observed after 1 h more PPh3 in THF (1.2 eq), DIAD in THF (1.2 eq) and DPPA in THF (0.6 eq) were added at RT. The formation of a precipitate was observed. Stirring was continued for 1 h at RT after which time HPLC-MS indicated complete conversion. The mixture was used without further treatment in the next reaction (quant). (ES+) m/z 538 (M+H)+.

Workup

  1. waitThe mixture was left
  2. additionAfter complete addition the mixture
  3. stirringwas stirred at 0° C. for further 30 min
  4. stirringstirring
  5. customwas continued at RT
  6. waitSince no reaction was observed after 1 h
  7. stirringStirring
  8. waitwas continued for 1 h at RT
  9. customThe mixture was used without further treatment in the next reaction (quant)

Sources & evidence

ORD record
ord-8f5c7751db4e40ba92fcab87b344c71f
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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