Water → HCID 66590077, compound

HRID 1092807Notes

Reaction equation

HRID 1092807 reaction equation
[N:1]([CH2:4][C@@H:5]1[C:10]([C:11](=[O:25])[N:12]([CH:22]2[CH2:24][CH2:23]2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=2[Cl:21])=[C:9]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][O:35][C:36]3[C:41]([Cl:42])=[CH:40][CH:39]=[CH:38][C:37]=3[Cl:43])=[CH:28][CH:27]=2)[CH2:8][CH2:7][N:6]1[C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][CH2:4][C@@H:5]1[C:10]([C:11](=[O:25])[N:12]([CH:22]2[CH2:24][CH2:23]2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=2[Cl:21])=[C:9]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][O:35][C:36]3[C:37]([Cl:43])=[CH:38][CH:39]=[CH:40][C:41]=3[Cl:42])=[CH:28][CH:27]=2)[CH2:8][CH2:7][N:6]1[C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86761502HCID 86761502, compound

Product 1

HCID 66590077HCID 66590077, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 10 mL round bottom flask was added 19C (200 mg, 302 μmol) and THF (3 mL). Triphenylphosphine (166 mg, 634 μmol) and water (112 mg, 6.22 mmol) was added and the flask was fitted with a reflux condenser and nitrogen inlet. The mixture was refluxed for three hours. Solvent was removed under vacuum and the residue was purified by preparatory LCMS to give 19D (40 mg, 21%). ESI-MS:m/z 734.2 (M+H)+.

Workup

  1. customthe flask was fitted with a reflux condenser and nitrogen inlet
  2. temperatureThe mixture was refluxed for three hours
  3. customSolvent was removed under vacuum
  4. customthe residue was purified by preparatory LCMS

Sources & evidence

ORD record
ord-d4ca712d7c494275bd067d6196937fcd
Source dataset
uspto-grants-2012_03
Patent number
US08129538B1

Reaction notes

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