Water → HCID 69640848, compound

HRID 1744216Notes

Reaction equation

HRID 1744216 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C@@H:18]([OH:27])[CH2:17][C@H:16]4[C:28]#N)[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:30].[K+].[OH2:32]>C(O)CO>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C@@H:18]([OH:27])[CH2:17][C@@H:16]4[C:28]([OH:32])=[O:30])[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 14797Potassium HydroxideHCID 69640587HCID 69640587, compound

Product 1

HCID 69640848HCID 69640848, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
160 °C

Procedure

A solution of 571 mg (1.47 mmol) of 46 crude, 2.54 g (45.3 mmol) KOH in H2O (6 mL) and ethylene glycol (34 mL) was stirred and heated at 160° C. for 112 h without a reflux condenser to allow H2O to evaporate. The reaction mixture was poured into H2O (700 mL) and washed with Et2O (2×, 100 mL). The aqueous phase was adjusted to pH 2 with concentrated HCl and extracted with Et2O (3×, 100 mL). Combined organic extracts were washed with 10% sodium metabisulfite (50 mL), H2O (50 mL), dried over Na2SO4 and concentrated in vacuo giving 535 mg (89%, two steps) of 47 as a tan solid. Data for 47: TLC, T-3, Rf 0.575; 1H NMR (400 MHz, DMSO-d6) 60.69 (s, 3H, H-18), 3.61 (ddd, 1H, J=8.7, 8.7, 5.0 Hz, H-17α), 4.73 (d, 1H, J=5.0 Hz, 17-OH), 5.04 (s, 2H, benzylic-H), 6.67 (d, 1H, J=2.6 Hz, H-4), 6.74 (dd, 1H, J=8.7, 2.6 Hz, H-2), 7.17 (d, 1H, J=8.7 Hz, H-1), 7.31–7.42 (m, 5H, Ar—H), 12.07 (s, 1H, OH).

Workup

  1. customto evaporate
  2. additionThe reaction mixture was poured into H2O (700 mL)
  3. washwashed with Et2O (2×, 100 mL)
  4. extractionextracted with Et2O (3×, 100 mL)
  5. washCombined organic extracts were washed with 10% sodium metabisulfite (50 mL), H2O (50 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99af849ce1ac494480cf46fd21ed43f1
Source dataset
uspto-grants-2006_03
Patent number
US07015211B2

Reaction notes

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