Ethanol → Ethinylestradiol

HRID 879905

Reaction equation

HRID 879905 reaction equation
[CH3:1][C@@:2]12[C@@H:18]([OH:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.[CH2:21](O)[CH3:22]>P([O-])([O-])([O-])=O>[CH3:1][C@@:2]12[C@:18]([OH:19])([C:21]#[CH:22])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2

Participants

4

Reactant 2

HCID 702EthanolHCID 5757Estradiol

Product 1

HCID 5991Ethinylestradiol

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Conditions

Temperature
37 °C

Procedure

Estradiol conjugate (33.5 mg, 0.039 mmol), prepared from Conjugate 1 as described in Example 16, was dissolved in 58 mL of a 9:4 ethanol/0.05 M aqueous phosphate buffer (pH 7.4) mixture, and the solution was shaken in a 37° C. incubator for 9 days. Six 8 mL aliquots were collected at 1-, 2-, 3-, 5-, 7-, and 9-day intervals. Estradiol release was quantified by adding 33 μL of a 0.09 M solution of butylated hydroxytoluene (BHT) in deuterochloroform as an internal standard, then comparing integrals of 1H NMR signals corresponding to the steroid and the internal standard. Results are shown in Table 4 below.

Workup

  1. customSix 8 mL aliquots were collected at 1-, 2-, 3-, 5-, 7-, and 9-day intervals
  2. additionby adding 33 μL of a 0.09 M solution of butylated hydroxytoluene (BHT) in deuterochloroform as an internal standard
  3. customResults

Sources & evidence

ORD record
ord-7a8a9a94b78c43e189ad97367162b27d
Source dataset
uspto-grants-2015_03
Patent number
US08992977B2

Linked notes

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