Acetic Anhydride → HCID 70477487, compound

HRID 462440Notes

Reaction equation

HRID 462440 reaction equation
[CH2:1]([O:3][C@H:4]1[CH2:21][C@@:20]2([CH3:22])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[C@H:18]([NH:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:29]([O:31][CH3:32])=[O:30])[CH2:6][C@@H:5]1[OH:33])[CH3:2].[C:34](OC(=O)C)(=[O:36])[CH3:35]>C(Cl)(Cl)Cl.C(O)C.C(OCC)(=O)C>[C:34]([O:33][C@@H:5]1[C@@H:4]([O:3][CH2:1][CH3:2])[CH2:21][C@@:20]2([CH3:22])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[C@H:18]([NH:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:29]([O:31][CH3:32])=[O:30])[CH2:6]1)(=[O:36])[CH3:35]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 12804575HCID 12804575, compound

Product 1

HCID 70477487HCID 70477487, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2β-ethoxy-3α-hydroxy-11α-(3-methylbutylamino)-5α-androstane-17β-carboxylate (464 mg) in chloroform containing dry PTSA (344 mg) was stirred for 20 min, then treated with acetic anhydride (1.0 ml) and the mixture left for 3 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×), water (1×), dried and evaporated to give an oil. This was purified by preparative t.l.c. in CHCl3 /MeOH (20:1) to give the title compound as an oil (415 mg), [α]D +27.9°, νmax 1725 cm-1.

Workup

  1. customevaporated
  2. customto give an oil
  3. washwashed with dilute ammonia solution (2×), water (1×)
  4. customdried
  5. customevaporated
  6. customto give an oil
  7. customThis was purified by preparative t.l.c

Sources & evidence

ORD record
ord-95734e5f188845df98d6a2255b0ac783
Source dataset
uspto-grants-1985_05
Patent number
US04515786

Reaction notes

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