HCID 86747686, compound → HCID 57175590, compound

HRID 487829Notes

Reaction equation

HRID 487829 reaction equation
[OH:1][C:2]12[O:32][CH:25]([CH:26]([O:30][CH3:31])[CH2:27][CH:28]1[CH3:29])[CH:24]([O:33][CH3:34])[CH2:23][CH:22]([CH3:35])[CH2:21][C:20]([CH3:36])=[CH:19][CH:18]([CH2:37][CH2:38][CH3:39])[C:17](=[O:40])[CH2:16][CH2:15][CH:14]([CH3:41])[CH:13]([C:42]([CH3:60])=[CH:43][CH:44]1[CH2:49][CH2:48][CH:47]([O:50]S(C(F)(F)F)(=O)=O)[CH:46]([O:58][CH3:59])[CH2:45]1)[O:12][C:11](=[O:61])[CH:10]1[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]1)[C:4](=[O:62])[C:3]2=[O:63]>ClCCl>[OH:1][C:2]12[O:32][CH:25]([CH:26]([O:30][CH3:31])[CH2:27][CH:28]1[CH3:29])[CH:24]([O:33][CH3:34])[CH2:23][CH:22]([CH3:35])[CH2:21][C:20]([CH3:36])=[CH:19][CH:18]([CH2:37][CH2:38][CH3:39])[C:17](=[O:40])[CH2:16][CH2:15][CH:14]([CH3:41])[CH:13]([C:42]([CH3:60])=[CH:43][CH:44]1[CH2:49][CH2:48][C@H:47]([OH:50])[CH:46]([O:58][CH3:59])[CH2:45]1)[O:12][C:11](=[O:61])[CH:10]1[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]1)[C:4](=[O:62])[C:3]2=[O:63]

Participants

3

Reactant 1

HCID 86747686HCID 86747686, compound

Product 1

HCID 57175590HCID 57175590, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Silica (18 g, Merck Kieselgel 60) was added to a solution of the product of step (a) (300 mg) in dichloromethane (100 ml). Volatiles were then removed in vacuo at room temperature and the resulting freely flowing powder was stored at 8° C. for 16 hours. The support was then washed with acetone containing triethylamine and the solvent was evaporated in vacuo to an oil. Chromatography on silica eluting with hexane in an acetone gradient then gave the title compound as a foam (79 mg).

Workup

  1. customVolatiles were then removed in vacuo at room temperature
  2. washThe support was then washed with acetone
  3. additioncontaining triethylamine
  4. customthe solvent was evaporated in vacuo to an oil

Sources & evidence

ORD record
ord-f0a90eae23394d24938b2ace2c0bb78b
Source dataset
uspto-grants-1994_03
Patent number
US05296489

Reaction notes

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