HCID 131719519, compound → HCID 56990074, compound

HRID 1079271Notes

Reaction equation

HRID 1079271 reaction equation
[CH2:1]([CH:3]1[CH2:29][CH:28]2[N:6]([C:7](=[O:82])[C:8](=[O:81])[C:9]3([OH:80])[O:76][CH:13]([CH:14]([O:74][CH3:75])[CH2:15][CH:16]([CH3:73])[CH2:17][C:18]([CH3:72])=[CH:19][CH2:20][C:21](=[O:71])[CH2:22][CH:23]([O:63][Si](C(C)(C)C)(C)C)[CH:24]([CH3:62])[CH:25]([C:31]([CH3:61])=[CH:32][CH:33]4[CH2:38][CH2:37][C:36]([O:51][Si](CC)(CC)CC)([CH2:39][CH2:40][CH:41]([C:43]5[CH:48]=[C:47]([CH3:49])[CH:46]=[C:45]([CH3:50])[CH:44]=5)[OH:42])[CH:35]([O:59][CH3:60])[CH2:34]4)[O:26][C:27]2=[O:30])[CH:12]([O:77][CH3:78])[CH2:11][CH:10]3[CH3:79])[CH2:5][CH2:4]1)[CH3:2]>C(#N)C>[CH2:1]([CH:3]1[CH2:29][CH:28]2[N:6]([C:7](=[O:82])[C:8](=[O:81])[C:9]3([OH:80])[O:76][CH:13]([CH:14]([O:74][CH3:75])[CH2:15][CH:16]([CH3:73])[CH2:17][C:18]([CH3:72])=[CH:19][CH2:20][C:21](=[O:71])[CH2:22][CH:23]([OH:63])[CH:24]([CH3:62])[CH:25]([C:31]([CH3:61])=[CH:32][CH:33]4[CH2:38][CH2:37][C:36]([OH:51])([CH2:39][CH2:40][CH:41]([C:43]5[CH:48]=[C:47]([CH3:49])[CH:46]=[C:45]([CH3:50])[CH:44]=5)[OH:42])[CH:35]([O:59][CH3:60])[CH2:34]4)[O:26][C:27]2=[O:30])[CH:12]([O:77][CH3:78])[CH2:11][CH:10]3[CH3:79])[CH2:5][CH2:4]1)[CH3:2]

Participants

3

Reactant 1

HCID 131719519HCID 131719519, compound

Product 1

HCID 56990074HCID 56990074, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 220 mg (0.186 mmole) of 7-ethyl-1-hydroxy-12-[2'-(4"-triethylsilyloxy-4"-[3-(3,5-dimethylphenyl)-3-hydroxypropyl]-3"-methoxycyclohexyl)-1'-methylvinyl]-14-t-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 10 mL of a 10% HF-acetonitrile solution was stirred at room temperature. After 18 h, the reaction was quenched with 5 mL of ethoxytrimethylsilane and the solution was concentrated. The oily residue was purified by HPLC (Waters RCM silica gel, 25×100 mm) using hexane-methyl t-butyl ether-acetonitrile (6:3:1) to afford 45 mg of the faster diastereomer as a white solid. MASS: 960 (M+Li)

Workup

  1. customthe reaction was quenched with 5 mL of ethoxytrimethylsilane
  2. concentrationthe solution was concentrated
  3. customThe oily residue was purified by HPLC (Waters RCM silica gel, 25×100 mm)
  4. customto afford 45 mg of the faster diastereomer as a white solid

Sources & evidence

ORD record
ord-67244a9ea53f4ba78b83c724a07986c6
Source dataset
uspto-grants-1996_08
Patent number
US05550233

Reaction notes

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