Hydrochloric Acid → HCID 86748202, compound

HRID 1708583Notes

Reaction equation

HRID 1708583 reaction equation
[H-].[K+].[CH3:3][C@H:4]1[C@H:9]2[C@H:10]3[C@H:20]([CH2:21][CH2:22][C@:7]2([CH3:8])[C@@H:6]([OH:24])[CH2:5]1)[C@:18]1([CH3:19])[C:13]([NH:14][C:15](=[O:23])[CH2:16][CH2:17]1)=[CH:12][CH2:11]3.[CH2:25](Br)[CH:26]=[CH2:27].Cl>>[CH3:3][C@H:4]1[C@H:9]2[C@H:10]3[C@H:20]([CH2:21][CH2:22][C@:7]2([CH3:8])[CH:6]([O:24][C:26](=[CH2:25])[CH3:27])[CH2:5]1)[C@:18]1([CH3:19])[C:13]([NH:14][C:15](=[O:23])[CH2:16][CH2:17]1)=[CH:12][CH2:11]3

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 82127Potassium hydrideHCID 15221160HCID 15221160, compound

Product 1

HCID 86748202HCID 86748202, compound

Procedure

Potassium hydride (40% oil dispersion, 114 mg, 2 mmol) was added to a 5 mL round bottomed flask fitted with a stirrer bar and a rubber septum. The potassium hydride dispersion was washed with dry hexane (2×5 ml) to remove the mineral oil and 3 mL of dry dimethylformamide was added to the flask. Azasteroid (11) (158 mg, 0.5 mmol) was added to the dispersion and the solution stirred at 0° under nitrogen for 1 h. Then allyl bromide (183 mg, 1.5 mmol) was syringed into the solution and the mixture stirred for 2 h at room temperature. The entire solution was poured into 5 mL of 1N HCl and the mixture extracted with 5×2 mL of dichloromethane. The pooled organic layer was washed with 3×5 mL of saturated brine. The product was flash chromatographed with 3/1 dichloromethane/ethyl acetate. Recovered product (78 mg, 0.2 mmol, 44%) δH (CDCl3) 0.89 (s, 3H), 0.99 (d, J=7 Hz,), 1.06 (s, 3H), 3.60 (m, J=7 Hz, 1H), 3.95 (dd, J=12 Hz, J=5 Hz), 4.64 (dd, J=12 Hz, J=5 Hz), 5.1 (m, 2H), 5.79 (m, 1H).

Workup

  1. customfitted with a stirrer bar
  2. washThe potassium hydride dispersion was washed with dry hexane (2×5 ml)
  3. customto remove the mineral oil and 3 mL of dry dimethylformamide
  4. additionwas added to the flask
  5. stirringthe mixture stirred for 2 h at room temperature
  6. extractionthe mixture extracted with 5×2 mL of dichloromethane
  7. washThe pooled organic layer was washed with 3×5 mL of saturated brine
  8. customchromatographed with 3/1 dichloromethane/ethyl acetate

Sources & evidence

ORD record
ord-436da0a3e4c4487da6a829acc9a613b1
Source dataset
uspto-grants-1994_10
Patent number
US05359071

Reaction notes

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