Hydrochloric Acid → HCID 86733143, compound

HRID 267629Notes

Reaction equation

HRID 267629 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[C:15](=[O:21])[CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:22]([O:24][CH3:25])=[O:23])[CH2:3]1.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1.O.Cl>N1C=CC=CC=1>[CH3:25][O:24][C:22]([C@H:11]1[CH2:10][CH2:9][C@H:8]2[C@H:7]3[C@H:16]([C:15](=[O:21])[CH2:14][C@:12]12[CH3:13])[C@:17]1([CH3:20])[C@H:4]([CH2:3][C@@H:2]([O:1][S:32]([C:29]2[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=2)(=[O:34])=[O:33])[CH2:19][CH2:18]1)[CH2:5][CH2:6]3)=[O:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 73974-Toluenesulfonyl chlorideHCID 867331443beta-Hydroxy-17beta-methoxycarbonyl-5alpha-androstan-11-one

Product 1

HCID 86733143HCID 86733143, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3β-Hydroxy-17β-methoxycarbonyl-5α-androstan-11-one (4.75 g.) and toluene-p-sulphonyl chloride (5 g.) in pyridine (50 ml.) were allowed to stand at room temperature for four days. Water (10 ml.) was added, the resulting solution was stirred for an hour and was then poured into stirred water (1.1). The mixture was acidified with hydrochloric acid and the product collected, washed well with water and dried over sodium hydroxide in vacuo. Recrystallisation from chloroform/hexane containing a trace of ether afforded pure title compound (3.4 g.) as needles; m.p. 158°-160°; [α]D + 42.5°, (c 1.09).

Workup

  1. additionwas then poured
  2. customthe product collected
  3. washwashed well with water
  4. dry with materialdried over sodium hydroxide in vacuo
  5. customRecrystallisation from chloroform/hexane containing a trace of ether afforded pure title compound (3.4 g.) as needles
  6. custom[α]D + 42.5°, (c 1.09)

Sources & evidence

ORD record
ord-02f42a44317341cdbe4e137c38d4bdbf
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

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