Dimethylcarbamoyl Chloride → HCID 22027791, compound

HRID 2220726Notes

Reaction equation

HRID 2220726 reaction equation
[C:1]([O:5][C:6]([O:8][NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:26][N:27]([CH3:31])[C:28](Cl)=[O:29].CCOC(C)=O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([O:5][C:6]([O:8][NH:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][C:28]([N:27]([CH3:31])[CH3:26])=[O:29])=[CH:16][CH:17]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 22027819HCID 22027819, compound

Product 1

HCID 22027791HCID 22027791, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

N-t-butoxycarbonyloxy 2-(4-hydroxyphenyl)ethylamine (2.53 g, 10.7 mmol), Et3N (2.96 mL, 2 eq.), a catalytic amount of DMAP (131 mg) and dimethylcarbamyl chloride (2.0 mL, 2 eq) are mixed in CH2Cl2 at 0° C. The resulting mixture is stirred overnight. EtOAc is added to dilute the reaction mixture and then is washed with 1N HCl, sat.Na2CO3 and brine. Solvent is removed under reduced pressure to give pure t-butoxycarbonyloxy 2-[4-(N,N-dimethylaminocarbonyloxy)phenyl]ethylamine as a solid.

Workup

  1. additionto dilute the reaction mixture
  2. washis washed with 1N HCl
  3. customSolvent is removed under reduced pressure

Sources & evidence

ORD record
ord-21119521ade6429bbd72649b70f1c4bd
Source dataset
uspto-grants-2008_08
Patent number
US07417152B2

Reaction notes

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