Triphenylphosphine → HCID 57262474, compound

HRID 2082618Notes

Reaction equation

HRID 2082618 reaction equation
[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH:27]([F:31])[CH:26]([CH3:32])[CH2:25][CH:24]([O:33][CH3:34])[CH:23]2[O:35][C:19]([OH:39])([CH:20]([CH3:38])[CH2:21][CH:22]2[O:36][CH3:37])[C:18](=[O:40])[C:17](=[O:41])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:42])[O:9][CH:8]([C:43]([CH3:56])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([N:51]=[N+]=[N-])[CH:47]([O:54][CH3:55])[CH2:46]2)[CH:7]([CH3:57])[CH2:6][CH2:5][C:4]1=[O:58])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[OH-:9].[NH4+:16].[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH:27]([F:31])[CH:26]([CH3:32])[CH2:25][CH:24]([O:33][CH3:34])[CH:23]2[O:35][C:19]([OH:39])([CH:20]([CH3:38])[CH2:21][CH:22]2[O:36][CH3:37])[C:18](=[O:40])[C:17](=[O:41])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:42])[O:9][CH:8]([C:43]([CH3:56])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([NH2:51])[CH:47]([O:54][CH3:55])[CH2:46]2)[CH:7]([CH3:57])[CH2:6][CH2:5][C:4]1=[O:58])[CH3:2]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 57075633HCID 57075633, compound

Product 2

HCID 14923Ammonium HydroxideYield 2%HCID 57262474HCID 57262474, compoundYield 161.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 17-ethyl-20-fluoro-1-hydroxy-12-[2'-(4"-azido-3"-methoxycyclohexyl)-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 (12 mg) in 10% aqueous benzene (0.5 ml) was added triphenylphosphine (4.2 mg) and the mixture heated to 70° C. with stirring. After 25 hours, the stir bar was removed and the reaction cooled to room temperature. The mixture was concentrated to 10% volume in vacuo and applied directly to a column of silica gel for purification by flash chromatography (ethyl acetate: hexane (1:1)+1% methanol then 2% ammonium hydroxide, 5% methanol in methylene chloride) to give the title compound (9.4 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. customapplied directly to a column of silica gel for purification by flash chromatography (ethyl acetate: hexane (1:1)+1% methanol

Sources & evidence

ORD record
ord-48391cb744304b9f8044b85c7c032674
Source dataset
uspto-grants-1993_02
Patent number
US05189042

Reaction notes

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