Triphenylphosphine → HCID 77372954, compound

HRID 257695Notes

Reaction equation

HRID 257695 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]([O:50][C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[CH:46]([N:57]=[N+]=[N-])[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]([O:50][C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[CH:46]([NH2:57])[CH2:45]2)[CH:7]([CH3:61])[CH2:6][CH2:5][C:4]1=[O:62])[CH3:2]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 57157478HCID 57157478, compound

Product 1

HCID 77372954HCID 77372954, compoundYield 21.5%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent

Procedure

17-Ethyl-1-hydroxy-12-[2'-(3"-azido-4"-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 (24 mg) in THF (1 ml) containing 1 drop of water was treated with triphenylphosphine (9 mg) and the mixture stirred at room temperature for 72 hours. The reaction mixture was purified directly by preparative thin layer chromatography eluting eith 90% dichloromethane:10% methanol to give the title compound (5 mg, 20%) 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 eith 90% dichloromethane

Sources & evidence

ORD record
ord-8dee24ea712743bf8cc47bc1c4d07302
Source dataset
uspto-grants-1993_11
Patent number
US05262533

Reaction notes

Loading…