Triethylamine → (R)-3-tert-butoxycarbonylamino-N,N-dimethyl-succinamic acid benzyl ester

HRID 1188208Notes

Reaction equation

HRID 1188208 reaction equation
[CH2:1]([N:3](CC)[CH2:4]C)C.[CH2:8]([O:15][C:16](=[O:30])[CH2:17][C@H:18]([C:27](O)=[O:28])[NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.ClC(OCC)=O.Cl.CNC>ClCCl>[CH2:8]([O:15][C:16](=[O:30])[CH2:17][C@@H:18]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:27]([N:3]([CH3:4])[CH3:1])=[O:28])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 10473Dimethylamine, hydrochlorideHCID 10928Ethyl chloroformateHCID 6994663Boc-D-Asp(OBzl)-OH

Product 1

HCID 68990953(R)-3-tert-butoxycarbonylamino-N,N-dimethyl-succinamic acid benzyl esterYield 71.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Triethylamine (2.8 mL, 20.0 mmol) was added at 0° C. to a solution of Boc-D-aspartic acid 4-benzyl ester (5.00 g, 15.0 mmol) in dichloromethane, then ethyl chloroformate (1.91 mL, 20.0 mmol) was added dropwise. The reaction mixture was stirred for 1 h at 0° C., then a solution of dimethylamine hydrochloride (2.65 g, 32.0 mmol) and triethylamine (4.53 mL, 32.0 mmol) in dichloromethane (100 mL) were added dropwise. The reaction mixture was allowed to reach room temperature over 16 h, then washed with brine, and concentrated. Chromatography (SiO2; heptane-ethyl acetate gradient) produced (R)-3-tert-butoxycarbonylamino-N,N-dimethyl-succinamic acid benzyl ester (3.77 g, 70%). Colorless oil, m/e=351.4 ([M+H]+).

Workup

  1. waitto reach room temperature over 16 h
  2. washwashed with brine
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4f5689d499a7498b9efc0494a0776da8
Source dataset
uspto-grants-2014_03
Patent number
US08673946B2

Reaction notes

Loading…