Methanol → HCID 70614731, compound

HRID 2419624Notes

Reaction equation

HRID 2419624 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([C@@H:10]1[C@:27]2([CH3:28])[C@H:13]([C@H:14]3[C@H:24]([CH2:25][C@@H:26]2[O:29]C=O)[C@:22]2([CH3:23])[C@@H:17]([CH2:18][C@H:19]([O:32]C=O)[CH2:20][CH2:21]2)[CH2:16][CH2:15]3)[CH2:12][CH2:11]1)[CH3:9].CO.[OH-].[Na+]>O>[OH:32][C@@H:19]1[CH2:20][CH2:21][C@@:22]2([CH3:23])[C@H:17]([CH2:16][CH2:15][C@@H:14]3[C@@H:24]2[CH2:25][C@H:26]([OH:29])[C@@:27]2([CH3:28])[C@H:13]3[CH2:12][CH2:11][C@@H:10]2[CH:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:35])=[O:2])[CH3:9])[CH2:18]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86735946HCID 86735946, compound

Product 1

HCID 70614731HCID 70614731, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 7.2 g of 5-(3α,12α-diformyloxy-5β-pregnane-20-yl)pentanoic acid methyl ester, 50 ml of methanol, 50 ml of 2N methanolic sodium hydroxide solution and 10 ml of water was refluxed for 2 hr. At the end of this time, the methanol was removed under reduced pressure and 300 ml of water was added to the residue. The solution was treated with charcoal and filtered through a bed of diatomaceous earth. The solution was then cooled to 0° and with stirring acidified (pH3) by the dropwise addition of concentrated aqueous hydrochloric acid. The precipitate was filtered and dried overnight under house vacuum. Crystallization from methyl ethyl ketone gave 4 g of 5-(3α,12α-dihydroxy-5β-pregnane-20-yl)pentanoic acid, mp 191°-193°.

Workup

  1. customAt the end of this time, the methanol was removed under reduced pressure and 300 ml of water
  2. additionwas added to the residue
  3. additionThe solution was treated with charcoal
  4. filtrationfiltered through a bed of diatomaceous earth
  5. temperatureThe solution was then cooled to 0°
  6. additionby the dropwise addition of concentrated aqueous hydrochloric acid
  7. filtrationThe precipitate was filtered
  8. customdried overnight under house vacuum
  9. customCrystallization from methyl ethyl ketone

Sources & evidence

ORD record
ord-bdf49abf269e49d9ab4afe0360e250a3
Source dataset
uspto-grants-1978_08
Patent number
US04107188

Reaction notes

Loading…