Ethanol → HCID 70477852, compound

HRID 462441Notes

Reaction equation

HRID 462441 reaction equation
[CH:1]1([NH:7][C@@H:8]2[CH2:25][C@@:23]3([CH3:24])[C@@H:19]([CH2:20][CH2:21][C@@H:22]3[C:26]([O:28][CH3:29])=[O:27])[C@H:18]3[C@H:9]2[C@:10]2([CH3:31])[C@@H:15]([CH2:16][CH2:17]3)[CH2:14][C@H:13]([OH:30])[CH2:12][CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC1C=CC(S(O)(=O)=O)=CC=1.[CH3:43][C:44](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:45].[CH2:67]([OH:69])C>C(Cl)(Cl)Cl.C(OCC)(=O)C>[C:44]([O:30][C@@H:13]1[C@@H:12]([O:69][CH3:67])[CH2:11][C@@:10]2([CH3:31])[C@@H:15]([CH2:16][CH2:17][C@@H:18]3[C@@H:9]2[C@H:8]([NH:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:25][C@@:23]2([CH3:24])[C@H:19]3[CH2:20][CH2:21][C@@H:22]2[C:26]([O:28][CH3:29])=[O:27])[CH2:14]1)(=[O:45])[CH3:43]

Participants

7

Reactant 4

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 12804606HCID 12804606, compound

Product 1

HCID 70477852HCID 70477852, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 11α-cyclohexylamino-3α-hydroxy-5α-androstane-17β-carboxylate (740 mg) in chloroform (8 ml) containing dry PTSA (640 mg) was stirred for 20 min then treated with acetic anhyride (1.9 ml) and left for 20 h. The reaction mixture was diluted with ethanol and evaporated to give an oil. This was dissolved in ethyl acetate, washed with dilute ammonia solution (2×) and water (1×), dried and evaporated to give a foam. This was purified by preparative t.l.c. in chloroform/methanol (9:1) to give a foam which was crystallised from acetonitrile to give the title compound, m.p. 87°-89° [α]D +16.9°.

Workup

  1. waitleft for 20 h
  2. customevaporated
  3. customto give an oil
  4. washwashed with dilute ammonia solution (2×) and water (1×)
  5. customdried
  6. customevaporated
  7. customto give a foam
  8. customThis was purified by preparative t.l.c
  9. customin chloroform/methanol (9:1) to give a foam which
  10. customwas crystallised from acetonitrile

Sources & evidence

ORD record
ord-755fcf2e9eb34dda9817568692988675
Source dataset
uspto-grants-1985_05
Patent number
US04515786

Reaction notes

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