Triphenylphosphine → HCID 86614779, compound

HRID 643839Notes

Reaction equation

HRID 643839 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][C@@H:11]([OH:13])[CH2:10][C@H:9]1[C:14](=[O:26])[NH:15][C@:16]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:18][C@H:17]1[CH:19]=[CH2:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:27]([NH:30][C:31]1[S:32][CH:33]=[C:34]([C:36]2[CH:45]=[C:44](O)[C:43]3[C:38](=[CH:39][C:40]([O:47][CH3:48])=[CH:41][CH:42]=3)[N:37]=2)[N:35]=1)([CH3:29])[CH3:28].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:24]([O:23][C:21]([C@@:16]1([NH:15][C:14]([C@@H:9]2[CH2:10][C@@H:11]([O:13][C:44]3[C:43]4[C:38](=[CH:39][C:40]([O:47][CH3:48])=[CH:41][CH:42]=4)[N:37]=[C:36]([C:34]4[N:35]=[C:31]([NH:30][CH:27]([CH3:29])[CH3:28])[S:32][CH:33]=4)[CH:45]=3)[CH2:12][C@H:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:26])[CH2:18][CH:17]1[CH:19]=[CH2:20])=[O:22])[CH3:25]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 59165438(1R,2R,4S)-2-((1R,2S)-1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl) 4-hydroxy-cyclopentanecarboxylic acid tert-butyl esterHCID 178487686HCID 178487686, compound

Product 1

HCID 86614779HCID 86614779, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 35 (0.10 mmol) in dry THF (4 mL) was added the quinoline 12 (0.16 mmol) and Ph3P (0.40 mmol). After cooling to 0° C. DIAD (0.40 mmol) was added dropwise during 5 min. The solution was stirred at 0° C. for 1 h and at rt for 48 h. The solvent was evaporated and the remainder was purified using flash column chromatography (toluene/EtOAc 1:1) to give the title compound (10%) as a white solid.

Workup

  1. customThe solvent was evaporated
  2. customthe remainder was purified

Sources & evidence

ORD record
ord-1e7eda70a128453cb80f0ac15dc05079
Source dataset
uspto-grants-2010_04
Patent number
US07700552B2

Reaction notes

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