Triphenylphosphine → HCID 56997118, compound

HRID 257696Notes

Reaction equation

HRID 257696 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]([CH3:60])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([N:50]=[N+]=[N-])[CH:46]([O:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[CH2:45]2)[CH:7]([CH3:61])[CH2:6][CH2:5][C:4]1=[O:62])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[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]([CH3:60])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([NH2:50])[CH:46]([O:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[CH2:45]2)[CH:7]([CH3:61])[CH2:6][CH2:5][C:4]1=[O:62])[CH3:2]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 86747382HCID 86747382, compound

Product 1

HCID 56997118HCID 56997118, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent

Procedure

17-Ethyl-1-hydroxy-12-[2'-(4"-azido-3"-phenoxycyclohexyl)-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 (64 mg) in THF (1.5 mml) containing 1 drop of water was treated with triphenylphosphine (24 mg) and the mixture stirred at room temperature for 72 hours. The reaction mixture was purified directly by preparative thin layer chromatography eluting with 90% dichloromethane:10% methanol to give the title compound (43 mg, 68%) as a white solid. (1H NMR analysis was consistent with the desired structure).

Workup

  1. customThe reaction mixture was purified directly by preparative thin layer chromatography
  2. washeluting with 90% dichloromethane

Sources & evidence

ORD record
ord-57e468ca48d14d6ba91ddd486180b1f4
Source dataset
uspto-grants-1993_11
Patent number
US05262533

Reaction notes

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