HCID 131719518, compound → HCID 57231209, compound

HRID 1079267Notes

Reaction equation

HRID 1079267 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]([CH3:64])=[CH:43][CH:44]2[CH2:49][CH2:48][C:47]([OH:61])([CH2:50][C:51]([O:53][CH2:54][C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)=[O:52])[CH:46]([O:62][CH3:63])[CH2:45]2)[CH:7]([CH3:65])[CH:6]([O:66][Si](C(C)(C)C)(C)C)[CH2:5][C:4]1=[O:74])[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]([CH3:64])=[CH:43][CH:44]2[CH2:49][CH2:48][C:47]([OH:61])([CH2:50][C:51]([O:53][CH2:54][C:55]3[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=3)=[O:52])[CH:46]([O:62][CH3:63])[CH2:45]2)[CH:7]([CH3:65])[CH:6]([OH:66])[CH2:5][C:4]1=[O:74])[CH3:2]

Participants

3

Reactant 1

HCID 131719518HCID 131719518, compound

Product 1

HCID 57231209HCID 57231209, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.200 g (0.191 mmole) of 17-ethyl-1-hydroxy-12-[2'-(4"-hydroxy-4"-[benzyloxycarbonylmethyl]-3"-methoxycyclohexyl)-1'-methylvinyl]-14-tert-butyldimethylsilyloxy-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 in 5 mL of 10% (48% aqueous HF)-acetonitrile was stirred at room temperature for 16 h. The reaction was quenched by addition of 5 mL of trimethylethoxy-silane and the solution was concentrated under vacuum. The residue was purified by flash chromatography (silica gel, 1.5 cm×10 cm) using acetone-hexane and the product lyophilized from benzene to afford 0.148 g (82%) of the title compound as a colorless solid; MS (FAB) 946 (M+Li).

Workup

  1. customThe reaction was quenched by addition of 5 mL of trimethylethoxy-silane
  2. concentrationthe solution was concentrated under vacuum
  3. customThe residue was purified by flash chromatography (silica gel, 1.5 cm×10 cm)

Sources & evidence

ORD record
ord-50a127e2156d438f901ce485b2c745b7
Source dataset
uspto-grants-1996_08
Patent number
US05550233

Reaction notes

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