Acetone → HCID 131719512, compound

HRID 1079262Notes

Reaction equation

HRID 1079262 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]([CH3:70])=[CH:43][CH:44]2[CH2:49][CH2:48][C:47]([O:60][Si:61]([CH2:66][CH3:67])([CH2:64][CH3:65])[CH2:62][CH3:63])([CH2:50][CH2:51][CH:52]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[OH:53])[CH:46]([O:68][CH3:69])[CH2:45]2)[CH:7]([CH3:71])[CH:6]([O:72][Si:73]([C:76]([CH3:79])([CH3:78])[CH3:77])([CH3:75])[CH3:74])[CH2:5][C:4]1=[O:80])[CH3:2].CC([O-])=O.[Na+].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.CC(C)=O>C(Cl)Cl.C(OCC)C.CCCCCC>[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]([CH3:70])=[CH:43][CH:44]2[CH2:49][CH2:48][C:47]([O:60][Si:61]([CH2:66][CH3:67])([CH2:62][CH3:63])[CH2:64][CH3:65])([CH2:50][CH2:51][C:52]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)=[O:53])[CH:46]([O:68][CH3:69])[CH2:45]2)[CH:7]([CH3:71])[CH:6]([O:72][Si:73]([C:76]([CH3:77])([CH3:79])[CH3:78])([CH3:74])[CH3:75])[CH2:5][C:4]1=[O:80])[CH3:2]

Participants

8

Reactant 4

HCID 180AcetoneHCID 517045Sodium AcetateHCID 131719513HCID 131719513, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 131719512HCID 131719512, compoundYield 57.8%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a solution of 17-ethyl-1-hydroxy-12-[2'-(4"-triethylsilyloxy-4"-[3-phenyl-3-hydroxypropyl]-3"-methoxycyclohexyl)-1'-methylvinyl]-14-t-butyl-dimethylsilyloxy-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 (10 mg, 0.009 mmole) in CH2Cl2 (2 mL) was added NaOAc (1.6 mg, 0.020 mmole) and PCC (3 mg, 0.014 mmole). The reaction mixture was then stirred 1 hour at room temperature when reaction was complete (TLC, silica, 1:4 acetone: hexane). Celite was added and the reaction was diluted with diethyl ether. After 20 min. the reaction mixture was filtered and concentrated in vacuo to give 6 mg of the title compound. MASS:(FAB) 1158(M+ + Li).

Workup

  1. customwhen reaction
  2. additionCelite was added
  3. filtrationAfter 20 min. the reaction mixture was filtered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-703f20906d2e4ec7a2faa6c6e1476993
Source dataset
uspto-grants-1996_08
Patent number
US05550233

Reaction notes

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