Acetone → HCID 131719509, compound

HRID 1079260Notes

Reaction equation

HRID 1079260 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]([CH3:57])=[CH:43][CH:44]2[CH2:49][CH2:48][C:47]([OH:54])([CH2:50][CH2:51][CH:52]=[CH2:53])[CH:46]([O:55][CH3:56])[CH2:45]2)[CH:7]([CH3:58])[CH:6]([O:59][Si:60]([C:63]([CH3:66])([CH3:65])[CH3:64])([CH3:62])[CH3:61])[CH2:5][C:4]1=[O:67])[CH3:2].N1C(C)=CC=CC=1C.[CH2:76]([Si:78](OS(C(F)(F)F)(=O)=O)([CH2:81][CH3:82])[CH2:79][CH3:80])[CH3:77].CC(C)=[O:93]>C(Cl)Cl.CO>[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]([CH3:57])=[CH:43][CH:44]2[CH2:49][CH2:48][C:47]([O:54][Si:78]([CH2:81][CH3:82])([CH2:79][CH3:80])[CH2:76][CH3:77])([CH2:50][CH2:51][CH:52]=[CH2:53])[CH:46]([O:55][CH3:56])[CH2:45]2)[CH:7]([CH3:58])[C:6]([OH:93])([O:59][Si:60]([C:63]([CH3:64])([CH3:65])[CH3:66])([CH3:61])[CH3:62])[CH2:5][C:4]1=[O:67])[CH3:2]

Participants

7

Reactant 4

HCID 180AcetoneHCID 79372,6-LutidineHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 57051401HCID 57051401, compound

Product 1

HCID 131719509HCID 131719509, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 17-ethyl-1-hydroxy-12-[2'-(4"-hydroxy-4"-[but-3-en-1-yl]-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 (0.9 gm, 0.94 mmol) in CH2Cl2 (25 ml) at room temperature was added 2,6-lutidine (0.33 mL) followed by triethylsilyltriflate (0.52 mL, 2.3 mmole) and the reaction mixture was stirred at room temperature. The reaction progress was monitored by TLC (silica, 20% acetone:hexanes). After 1 hr, the reaction was diluted with CH3OH and partitioned between diethyl ether and H2O. The organic layer was washed successively with 1N H2SO4, H2O, NaHSO3 and brine solutions. The organic fraction was then dried over MgSO4, filtered and concentrated in vacuo to give the title compound (1.47 gm). MASS: (FAB) 1080 (M+ + Li).

Workup

  1. custompartitioned between diethyl ether and H2O
  2. washThe organic layer was washed successively with 1N H2SO4, H2O, NaHSO3 and brine solutions
  3. dry with materialThe organic fraction was then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a8105073be9442f3986c4bfc263ee415
Source dataset
uspto-grants-1996_08
Patent number
US05550233

Reaction notes

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