Hydrochloric Acid → (S)-tert-butyl 4-chloro-1-cyclohexyl-3-oxobutan-2-ylcarbamate

HRID 253558Notes

Reaction equation

HRID 253558 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:9](=[O:13])[CH:10]=[N+]=[N-])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:22].O1CCOCC1>CCOCC>[Cl:22][CH2:10][C:9](=[O:13])[C@@H:8]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86632797(S)-tert-butyl 1-cyclohexyl-4-diazo-3-oxobutan-2-ylcarbamate

Product 1

HCID 10063585(S)-tert-butyl 4-chloro-1-cyclohexyl-3-oxobutan-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of the crude (S)-tert-butyl 1-cyclohexyl-4-diazo-3-oxobutan-2-ylcarbamate (7 g, ˜65% pure) in anhydrous ether (150 mL) at 0° C. was added dropwise a solution of 3.65 N HCl in dioxane (4.1 mL, 0.015 mmol). The mixture was stirred until tlc showed the starting material had been consumed. Satd aq NaHCO3 was added and the organic layer was separated, washed with satd aq NaHCO3 and brine, and concentrated to afford a solution of crude (S)-tert-butyl 4-chloro-1-cyclohexyl-3-oxobutan-2-ylcarbamate (5.8 g), which was used in the next step without further purification.

Workup

  1. customhad been consumed
  2. additionSatd aq NaHCO3 was added
  3. customthe organic layer was separated
  4. washwashed with satd aq NaHCO3 and brine
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-21ba1a6383164a4a8c27599e92771c4f
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Reaction notes

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