p-Toluenesulfonic acid → HCID 57071647, compound

HRID 248258Notes

Reaction equation

HRID 248258 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]([CH3:53])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([NH2:50])[CH:46]([O:51]C)[CH2:45]2)[CH:7]([CH3:54])[CH2:6][CH2:5][C:4]1=[O:55])[CH3:2].[CH2:56]1[O:59][CH:57]1[CH3:58].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[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]([CH3:53])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([NH:50][CH2:56][CH:57]([OH:59])[CH3:58])[CH:46]([OH:51])[CH2:45]2)[CH:7]([CH3:54])[CH2:6][CH2:5][C:4]1=[O:55])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6378Propylene OxideHCID 74990172HCID 74990172, compound

Product 1

HCID 57071647HCID 57071647, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 17-ethyl-1-hydroxy-12-[2'-(4"-amino-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 (52 mg, Example 13) in dry methanol (1 ml) was added a large excess of propylene oxide (200 μl) followed by a catalytic amount of p-toluenesulfonic acid at room temperature. After stirring at this temperature for 20 h, the solution was concentrated and purified by preparative tlc on silica gel (1% NH4OH in 5% i-PrOH/CH2Cl2) to give 35 mg of the title compound.

Workup

  1. concentrationthe solution was concentrated
  2. custompurified by preparative tlc on silica gel (1% NH4OH in 5% i-PrOH/CH2Cl2)

Sources & evidence

ORD record
ord-dea10142f5fa46f2aed38552b999e30b
Source dataset
uspto-grants-1993_05
Patent number
US05208228

Reaction notes

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