HCID 57276360, compound → HCID 57207245, compound

HRID 2082631Notes

Reaction equation

HRID 2082631 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]([CH3:64])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([O:51][CH2:52][CH2:53][O:54][CH2:55][C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)[CH:47]([O:62][CH3:63])[CH2:46]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.C(OCC)(=O)C>[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]([CH3:64])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([O:51][CH2:52][CH2:53][O:54][CH2:55][C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)[CH:47]([O:62][CH3:63])[CH2:46]2)[CH:7]([CH3:65])[CH:6]([OH:66])[CH2:5][C:4]1=[O:74])[CH3:2]

Participants

4

Reactant 1

HCID 57276360HCID 57276360, compound

Product 1

HCID 57207245HCID 57207245, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 17-ethyl-20-fluoro-1-hydroxy-14-(tert-butyldimethylsiloxy)-12-[2'-(4"-(2-benzyloxyethoxy)-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-2,3,10,16tetraone (10 mg) in acetonitrile (500 μl) is added a solution of 2% HF in aqueous acetonitrile (200 μl), and the mixture is stirred at room temperature. After 2.5 hours, the solution is diluted with ethyl acetate, extracted with saturated sodium bicarbonate solution and the organic phase dried over magnesium sulfate. Purification of the concentrate by flash chromatography on silica gel gives the title compound.

Workup

  1. extractionextracted with saturated sodium bicarbonate solution
  2. dry with materialthe organic phase dried over magnesium sulfate
  3. customPurification of the
  4. concentrationconcentrate by flash chromatography on silica gel

Sources & evidence

ORD record
ord-988fb09ea3a44785931643ed11ba15b4
Source dataset
uspto-grants-1993_02
Patent number
US05189042

Reaction notes

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