Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl (2E)-((1R,4R,5S,8S,12R)-7-(4-cyano-3-(trifluoromethyl)phenyl)-4-methyl-6-oxo-9,13-dioxa-7-azatetracyclo[6.3.1.11,4.05,12]tridec-2-ylidene)acetate

HRID 563908Notes

Reaction equation

HRID 563908 reaction equation
O[C@H:2]1[CH2:12][C@@:11]2([CH3:14])[O:13][C@@:3]31[C@@H:15]1[C@@H:7]([N:8]([C:17]4[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([C:25]([F:28])([F:27])[F:26])[CH:18]=4)[C:9](=[O:16])[C@H:10]21)[O:6][CH2:5][CH2:4]3.[CH3:29][O:30][C:31](=[O:52])[CH:32]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[C:21]([C:20]1[CH:23]=[CH:24][C:17]([N:8]2[C@@H:7]3[C@@H:15]4[C@@H:10]([C@:11]5([CH3:14])[O:13][C@@:3]4([CH2:4][CH2:5][O:6]3)/[C:2](=[CH:32]/[C:31]([O:30][CH3:29])=[O:52])/[CH2:12]5)[C:9]2=[O:16])=[CH:18][C:19]=1[C:25]([F:26])([F:27])[F:28])#[N:22]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 59635881Benzonitrile, 4-((3aR,4S,6R,6aS,8aS,8bR)-octahydro-4-hydroxy-6-methyl-7-oxo-3a,6-epoxy-3ah-pyrano(2,3,4-cd)isoindol-8(4H)-yl)-2-(trifluoromethyl)-

Product 1

HCID 86649395Methyl (2E)-((1R,4R,5S,8S,12R)-7-(4-cyano-3-(trifluoromethyl)phenyl)-4-methyl-6-oxo-9,13-dioxa-7-azatetracyclo[6.3.1.11,4.05,12]tridec-2-ylidene)acetateYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 3 (50 mg, 0.128 mmol) in THF (2 mL) was added methyl(triphenylphosphoranylidene)acetate (51 mg, 0.153 mmol). The reaction mixture was stirred for 3 days and then concentrated in vacuo. The resulting residue was purified by ISCO column (4.0 g column, EtOAc/hexane=0-80%, 10 mL/min) to give Example 103 (40.5 mg, 71%) as a yellow solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was purified by ISCO column (4.0 g column, EtOAc/hexane=0-80%, 10 mL/min)

Sources & evidence

ORD record
ord-df01495722c646e3b6e55dacaddd1cdc
Source dataset
uspto-grants-2011_11
Patent number
US08067582B2

Reaction notes

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