Isopropyl chloroformate → HCID 86648403, compound

HRID 409473Notes

Reaction equation

HRID 409473 reaction equation
CS([O-])(=O)=O.[C:6]([CH2:8][C@H:9]([NH3+:12])[CH2:10][CH3:11])#[N:7].CCN(C(C)C)C(C)C.Cl[C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24]>ClCCl>[CH:26]([O:25][C:23](=[O:24])[NH:12][C@H:9]([CH2:10][CH3:11])[CH2:8][C:6]#[N:7])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformateHCID 81531DiisopropylethylamineHCID 11435489HCID 11435489, compound

Product 1

HCID 86648403HCID 86648403, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-2-cyano-1-ethylethylammonium methanesulfonate (50 mmol; 9.72 g) and DIPEA (105 mmol; 13.6 g) in dichloromethane (100 mL) is added isopropyl chloroformate (52.5 mmol; 6.43 g) at 0° C. The solution is warmed to room temperature and stirred for 4 hours. The reaction mixture is quenched with brine and extracted with dichloromethane. The organic layer is washed with aqueous 0.1M HCl, saturated aqueous NaHCO3 solution and then brine, dried over MgSO4, filtered concentrated under reduced pressure to give ((R)-2-cyano-1-ethyl-ethyl)-carbamic acid isopropyl ester (8.75 g, 95%); ESI-MS m/z: 185 [M++1], Retention time 1.60 min (condition A).

Workup

  1. customThe reaction mixture is quenched with brine
  2. extractionextracted with dichloromethane
  3. washThe organic layer is washed with aqueous 0.1M HCl, saturated aqueous NaHCO3 solution
  4. dry with materialbrine, dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3a2ec7ef57ed44119e17564d69369f88
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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