HCID 129225519, compound → HCID 131729885, compound

HRID 1255412Notes

Reaction equation

HRID 1255412 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[OH:5][C@H:6]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C@H:8]([CH2:9][CH2:10][C@@H:11]3[C:27]2=[CH:26][CH2:25][C@@:24]2([CH3:32])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[C@H:16]([CH3:23])[CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH2:7]1>CC(O)=O>[C:1]([OH:4])(=[O:3])[CH3:2].[OH:5][C@H:6]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C@H:8]([CH2:9][CH2:10][C@@H:11]3[C:27]2=[CH:26][C:25](=[O:3])[C@@:24]2([CH3:32])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[C@H:16]([CH3:23])[CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH2:7]1

Participants

3

Reactant 1

HCID 129225519HCID 129225519, compound

Product 1

HCID 131729885HCID 131729885, compoundYield 116.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

CrO3 (8.0 g, 100 wt %, 80.0 mmol) is added to a solution of Compound 1.19 (8.0 g, 18.6 mmol) in AcOH (150 mL). The resulting reaction mixture is heated at 60° C. for about 24-36 h. Upon complete disappearance of the precursor, acetic acid is evaporated under vacuum, and the crude material is dissolved in diethyl ether (400 mL). The organic layer is washed with water (2×100 mL), saturated brine solution (100 mL) and dried over MgSO4 (40 g). The solvent is removed under vacuum and the crude material is purified by column chromatography [49(W)×600(L) mm, 60-120 Mesh silica, 120 g] eluting with ethyl acetate/hexane (1:5) [10 mL fractions, 3 mL/min elution, monitored by TLC and detected with UV light (254 nm) lamp; Rf for Compound 1.20=0.28 and Rf for Compound 1.19=0.61 in EtOAc/Hexane (1:4)] to afford Compound 1.20 (5 g, 60.5% yield) as a colorless solid. Table 9 describes the measured properties of the product.

Workup

  1. customThe resulting reaction mixture
  2. customUpon complete disappearance of the precursor, acetic acid is evaporated under vacuum
  3. dissolutionthe crude material is dissolved in diethyl ether (400 mL)
  4. washThe organic layer is washed with water (2×100 mL), saturated brine solution (100 mL)
  5. dry with materialdried over MgSO4 (40 g)
  6. customThe solvent is removed under vacuum
  7. customthe crude material is purified by column chromatography [49(W)×600(L) mm, 60-120 Mesh silica, 120 g]
  8. washeluting with ethyl acetate/hexane (1:5) [10 mL fractions, 3 mL/min elution, monitored by TLC and detected with UV light (254 nm) lamp; Rf for Compound 1.20=0.28 and Rf for Compound 1.19=0.61 in EtOAc/Hexane (1:4)]

Sources & evidence

ORD record
ord-dd8c129575eb4f1a953ab38c98e615a3
Source dataset
uspto-grants-2013_06
Patent number
US08461140B2

Reaction notes

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