Pyridine → 7alpha-(N,N-dimethylcarbamoyloxy)-20-(5,5-dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregn-5-en-3beta-yl acetate

HRID 1708751Notes

Reaction equation

HRID 1708751 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:31]2[O:32][C@@H:30]2[C@@:29]2([CH3:33])[C:7](=[CH:8][C@@H:9]([OH:35])[C@@H:10]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:34])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[CH:15]([CH:17]2[O:22][CH2:21][C:20]([CH3:24])([CH3:23])[CH2:19][O:18]2)[CH3:16])[CH2:6]1)(=[O:3])[CH3:2].N1C=CC=CC=1.[CH3:42][N:43]([CH3:47])[C:44](Cl)=[O:45].C1(C)C=CC=CC=1>CN(C)C1C=CN=CC=1.C(Cl)Cl.C(OCC)(=O)C.CCCCCC>[C:1]([O:4][C@H:5]1[C@@H:31]2[O:32][C@@H:30]2[C@@:29]2([CH3:33])[C:7](=[CH:8][C@@H:9]([O:35][C:44](=[O:45])[N:43]([CH3:47])[CH3:42])[C@@H:10]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:34])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[CH:15]([CH:17]2[O:18][CH2:19][C:20]([CH3:23])([CH3:24])[CH2:21][O:22]2)[CH3:16])[CH2:6]1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 1049PyridineHCID 1140TolueneHCID 6598Dimethylcarbamoyl ChlorideHCID 8674580220-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha, 2alpha-epoxy-7alpha-hydroxypregna-5-en-3beta-yl acetate

Product 1

HCID 867458047alpha-(N,N-dimethylcarbamoyloxy)-20-(5,5-dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregn-5-en-3beta-yl acetateYield 70%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 49.0 mg (0.1 mole) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxy-7α-hydroxypregna-5-en-3β-yl acetate, 0.24 ml (3 mmoles) of pyridine, 0.5 mg (0.004 mmole) of 4-(dimethylamino)pyridine, 0.12 ml (1.3 mmoles) of N,N-dimethylcarbamoyl chloride and 10 ml of dry toluene was stirred at a temperature of 60° C. for 10 hours. The reaction mixture thus obtained was cooled to room temperature, diluted with 50 ml of methylene chloride, washed with water 3 times and finally washed with aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. Finally the residue was purified by silica gel chromatography (eluent:ethyl acetate-hexane=1:10, v/v) to recover 37 mg of 7α-(N,N-dimethylcarbamoyloxy)-20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregn-5-en-3β-yl acetate (yield: 70%).

Workup

  1. customThe reaction mixture thus obtained
  2. temperaturewas cooled to room temperature
  3. washwashed with water 3 times
  4. washfinally washed with aqueous sodium chloride solution
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customFinally the residue was purified by silica gel chromatography (eluent

Sources & evidence

ORD record
ord-76a930cc3a4c4e53bccf053985058d7c
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

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