Triphenylphosphine → HCID 57249267, compound

HRID 248272Notes

Reaction equation

HRID 248272 reaction equation
[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:57])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([N:50]=[N+]=[N-])[CH:46]([O:53][CH:54]([CH3:56])[CH3:55])[CH2:45]2)[CH:7]([CH3:58])[CH:6]([OH:59])[CH2:5][C:4]1=[O:60])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:57])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([NH2:50])[CH:46]([O:53][CH:54]([CH3:56])[CH3:55])[CH2:45]2)[CH:7]([CH3:58])[CH:6]([OH:59])[CH2:5][C:4]1=[O:60])[CH3:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 57012465HCID 57012465, compound

Product 1

HCID 57249267HCID 57249267, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 17-ethyl-1,14-dihydroxy-12-[2'-(4"-azido-3"-isopropyloxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (22 mg) in 10% aqueous toluene (0.5 ml) was added triphenylphosphine (10.7 mg) and the mixture heated to 70° C. with stirring. After 18 hours, the stir bar was removed and the reaction cooled to room temperature. The mixture was concentrated to 10% volume in vacuo and purified by preparative TLC on silica gel (2% ammonium hydroxide, 5% methanol in methylene chloride) to give the title compound (5.5 mg).

Workup

  1. customthe stir bar was removed
  2. temperaturethe reaction cooled to room temperature
  3. concentrationThe mixture was concentrated to 10% volume in vacuo
  4. custompurified by preparative TLC on silica gel (2% ammonium hydroxide, 5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-94448dcf6cc649c78a1d5263722dfa07
Source dataset
uspto-grants-1993_05
Patent number
US05208228

Reaction notes

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