Hydrochloric Acid → HCID 86746641, compound

HRID 1613977Notes

Reaction equation

HRID 1613977 reaction equation
[Na].Cl/[C:3](=[C:9]1\[CH2:10][CH2:11][C@@H:12]2[C@:26]\1([CH3:27])[CH2:25][CH2:24][C@@:23]1([OH:28])[C@H:13]2[CH2:14][CH:15]=[C:16]2[C@:21]1([CH3:22])[CH2:20][CH2:19][C:18]1([O:32][CH2:31][CH2:30][O:29]1)[CH2:17]2)/[C:4]([O:6][CH2:7]C)=[O:5].[OH2:33].Cl.[CH3:35]O>>[CH2:31]1[CH2:30][O:29][C:18]2([CH2:19][CH2:20][C@@:21]3([CH3:22])[C:16](=[CH:15][CH2:14][C@@H:13]4[C@:23]3([OH:28])[CH2:24][CH2:25][C@@:26]3([CH3:27])[C@H:12]4[CH2:11][CH2:10]/[C:9]/3=[C:3](/[O:33][CH3:35])\[C:4]([O:6][CH3:7])=[O:5])[CH2:17]2)[O:32]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 962Water2×HCID 5360545SodiumHCID 86746642HCID 86746642, compound

Product 1

HCID 86746641HCID 86746641, compound

Procedure

To a solution of sodium (171 mg) in anhydrous methanol (10 ml) was added ethyl (20E)-20-chloro-3,3-ethylenedioxy-9α-hydroxypregna-5,17(20)-dien-21-oate (306 mg, as prepared in example 18), after which the reaction mixture was refluxed under nitrogen for 21 hours. The reaction mixture was cooled to room temperature. After adding methanol (20 ml) and water (10 ml) the mixture was neutralised with aqueous 5N hydrochloric acid. More water (30 ml) was added and a precipitate was formed. The solid was filtered, washed with water and dried to afford 46 mg of the title compound as a single isomer.

Workup

  1. temperatureafter which the reaction mixture was refluxed under nitrogen for 21 hours
  2. customa precipitate was formed
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-c2942037d4f741919dce9fbd17d52afd
Source dataset
uspto-grants-1993_03
Patent number
US05194602

Reaction notes

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