Tert-Butyl nitrite → HCID 68405889, compound

HRID 1424983Notes

Reaction equation

HRID 1424983 reaction equation
C(OC(N(C(OC(C)(C)C)=O)[C:9]1[S:10][C:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:12]([C:14](=[O:17])[CH2:15][CH3:16])[N:13]=1)=O)(C)(C)C.[ClH:30].C(OCC)(=O)C.N(OC(C)(C)C)=O>CO.[Cu](Cl)Cl>[Cl:30][C:9]1[S:10][C:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:12]([C:14](=[O:17])[CH2:15][CH3:16])[N:13]=1

Participants

6

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 21866389Hydrogen chloride-ethyl acetateHCID 68406358HCID 68406358, compound

Product 1

HCID 68405889HCID 68405889, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 2-[bis(tert-butoxycarbonyl)amino]-4-propanoyl-1,3-thiazole-5-carboxylate obtained in Example (62f) (270.5 mg, 0.63 mmol) was dissolved in methanol (2 mL). A 4 N hydrochloric acid/ethyl acetate solution (6 mL) was added, and the mixture was stirred at 50° C. for 50 minutes. The reaction solution was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The same operation as in Example (22c) was performed using the resulting crude product, copper chloride (96 mg, 0.71 mmol) and tert-butyl nitrite (86 μL, 0.72 mmol), to obtain 49.0 mg of the title compound as a colorless oily substance (31%).

Workup

  1. washThe reaction solution was washed with saturated aqueous sodium bicarbonate solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-47396a2266e5403ebf9b71de2e9f1a1b
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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