Water → HCID 19049246, compound

HRID 1780016Notes

Reaction equation

HRID 1780016 reaction equation
C([O:8][C:9]1[CH:36]=[C:35]([OH:37])[C:12]2[C:13](=[O:34])[CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH2:26][C:27]4[O:28]C(C)(C)[O:30][CH:31]=4)[CH:18]=3)[O:16][C:11]=2[CH:10]=1)C1C=CC=CC=1.O.[CH2-]C(C)=O>C(O)(=O)C>[OH:37][C:35]1[C:12]2[C:13](=[O:34])[CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH2:26][CH:27]([OH:28])[CH2:31][OH:30])[CH:18]=3)[O:16][C:11]=2[CH:10]=[C:9]([OH:8])[CH:36]=1

Participants

5

Reactant 3

HCID 962WaterHCID 19049223HCID 19049223, compoundHCID 178477758HCID 178477758, compound

Product 1

HCID 19049246HCID 19049246, compoundYield 111.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

The 36 g of compound obtained in Example 9 are added to 200 ml of a mixture of water and acetic acid (1/1) and the whole is heated at reflux until the mixture becomes homogeneous, after which refluxing is maintained for a further 15 minutes. The disappearance of the acetonide is verified by thin-layer chromatography, then the mixture is cooled to 0° C., and the precipitate formed is filtered and then dried, yielding 30 g of the expected compound of 98% purity. Recrystallisation of that compound from a mixture of isopropanol and water yields the pure product, m.p.: 215°-218° C.

Workup

  1. temperaturethe whole is heated
  2. temperatureat reflux until the mixture
  3. temperatureafter which refluxing
  4. temperatureis maintained for a further 15 minutes
  5. customthe precipitate formed
  6. filtrationis filtered
  7. customdried

Sources & evidence

ORD record
ord-6e66659049a34a8da03ea9ec8652cfc2
Source dataset
uspto-grants-1997_05
Patent number
US05629339

Reaction notes

Loading…