HCID 53903901, compound → HCID 54250165, compound

HRID 1974954Notes

Reaction equation

HRID 1974954 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][Si](C(C)(C)C)(C)C)[CH:46]([O:58][CH3:59])[CH2:45]2)[CH:7]([CH3:61])[CH:6]([O:62][Si](C(C)(C)C)(C)C)[CH2:5][C:4]1([OH:71])[CH3:70])[CH3:2]>C(#N)C>[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]([OH:50])[CH:46]([O:58][CH3:59])[CH2:45]2)[CH:7]([CH3:61])[CH:6]([OH:62])[CH2:5][C:4]1([OH:71])[CH3:70])[CH3:2]

Participants

3

Reactant 1

HCID 53903901HCID 53903901, compound

Product 1

HCID 54250165HCID 54250165, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.086 g (0.082 mmole) of 17-ethyl-14-t-butyldimethylsilyloxy-1,16-dihydroxy-12-[2'-(4"-t-butyldimethylsilyloxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-16-methyl-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10-trione in 2 mL of a solution of 1:9 48% aqueous HF-acetonitrile was stirred at room temperature for 8 h. The reaction was quenched by addition of 2 mL of ethoxytrimethylsilane and the solution was concentrated to dryness under vacuum. The residue was purified by flash chromatography (2×20 cm silica gel) using 25% acetone-hexane to afford 0.051 g (77%) of the title compound as a white solid.

Workup

  1. customThe reaction was quenched by addition of 2 mL of ethoxytrimethylsilane
  2. concentrationthe solution was concentrated to dryness under vacuum
  3. customThe residue was purified by flash chromatography (2×20 cm silica gel)

Sources & evidence

ORD record
ord-1d41795194ae45d5ad667c6053b69386
Source dataset
uspto-grants-1994_02
Patent number
US05284840

Reaction notes

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