Sulfuric Acid → HCID 14698589, compound

HRID 846212Notes

Reaction equation

HRID 846212 reaction equation
[CH3:1][C:2]([C:5]1[CH:26]=[CH:25][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20](OCC)=[O:21])=[CH:14][CH:13]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.S(=O)(=O)(O)O>O>[CH3:4][C:2]([C:5]1[CH:26]=[CH:25][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][OH:21])=[CH:14][CH:13]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 14698592HCID 14698592, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14698589HCID 14698589, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.2 g. of the compound of Example 31 are reduced with 0.65 g. lithium aluminum hydride in 50 ml. boiling diethyl ether. The reaction mixture is mixed with water, sufficient 10% sulphuric acid is added thereto just to dissolve the precipitate, extracted with diethyl ether, evaporated to dryness and the remaining oil purified by column chromatography (silica gel; dichloromethane/methanol 99:1 v/v). The appropriate fractions are evaporated to dryness in a vacuum, the residue is first recrystallised from ethyl acetate/ligroin (1:1 v/v) and then from toluene to give 0.6 g. (31% of theory) of the title compound; m.p. 136°-142° C.

Workup

  1. additionis added
  2. dissolutionjust to dissolve the precipitate
  3. extractionextracted with diethyl ether
  4. customevaporated to dryness
  5. customthe remaining oil purified by column chromatography (silica gel; dichloromethane/methanol 99:1 v/v)
  6. customThe appropriate fractions are evaporated to dryness in a vacuum
  7. customthe residue is first recrystallised from ethyl acetate/ligroin (1:1 v/v)
  8. customfrom toluene to give 0.6 g

Sources & evidence

ORD record
ord-098980a05fcb4283b1431d7bc71a6412
Source dataset
uspto-grants-1992_08
Patent number
US05135949

Reaction notes

Loading…