Methanol → HCID 54369311, compound

HRID 1974956Notes

Reaction equation

HRID 1974956 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]([OH:50])[CH:46]([O:51][CH3:52])[CH2:45]2)[CH:7]([CH3:54])[CH:6]([OH:55])[CH2:5][C:4]1([OH:59])[CH2:56][S:57][CH3:58])[CH3:2].C[OH:61]>>[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]([OH:50])[CH:46]([O:51][CH3:52])[CH2:45]2)[CH:7]([CH3:54])[CH:6]([OH:55])[CH2:5][C:4]1([OH:59])[CH2:56][S:57]([CH3:58])=[O:61])[CH3:2]

Participants

3

Reactant 2

HCID 887MethanolHCID 54261402HCID 54261402, compound

Product 1

HCID 54369311HCID 54369311, compoundYield 44%

Procedure

A solution of 0.050 g (0.059 mmole) of 17-ethyl-1,14,16-trihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-16-(methylthiomethyl)-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10-trione in 5 mL of methanol was cooled to 0° C. in an ice bath. Then 2 mL of a 0.5M solution of NaIO4 was added and the mixture was stirred at room temperature for 1 h. The solution was partitioned between ether and water and the ether layer was washed with KHCO3 and brine, then dried over MgSO4 and concentrated. The residue was purified by flash chromatography (2×20 cm silica gel) using 20% acetone-hexane to afford 0.022 g (44%) of the title compound as a white solid; MASS SPECTRUM (FAB) m/e 876 (M+Li).

Workup

  1. customThe solution was partitioned between ether and water
  2. washthe ether layer was washed with KHCO3 and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (2×20 cm silica gel)

Sources & evidence

ORD record
ord-a97248572109480f92c9fdc09550da6f
Source dataset
uspto-grants-1994_02
Patent number
US05284840

Reaction notes

Loading…