Dimethylformamide → HCID 86688753, compound

HRID 400991Notes

Reaction equation

HRID 400991 reaction equation
[NH:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:2]([C:11](O)=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.C(=O)(O)[O-].[NH4+].C[N:42](C)C=O>C1(C)C=CC=CC=1.O.N1C=CC=CC=1>[NH2:42][C:11](=[O:12])[C@@H:2]([NH:1][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:3][C:4]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:10]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 14013Ammonium BicarbonateHCID 90495Di-tert-butyl dicarbonateHCID 70106364-(1,1-Dimethylethyl) hydrogen N-[(1,1-dimethylethoxy)carbonyl]-L-aspartate

Product 1

HCID 86688753HCID 86688753, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

360.0 g of the starting material, N-Boc-Asp(O-t-Bu)OH, together with Boc2O (353.0 g) and ammonium bicarbonate (NH4HCO3, 123.9 g) was added to dimethylformamide (1174.6 g), and pyridine (61.0 g) was added dropwise thereto at room temperature, and the reaction mixture was then stirred for about 3 hours. Upon completion of the reaction, water (1440 ml) and toluene (1800 ml) were added to the reaction solution and stirred for 30 minutes to separate the layers. The organic layer thus obtained was distilled under reduced pressure to remove t-butanol and toluene to obtain the title compound, which was directly used in the next reaction.

Workup

  1. additionwas added dropwise
  2. additionwere added to the reaction solution
  3. stirringstirred for 30 minutes
  4. customto separate the layers
  5. customThe organic layer thus obtained
  6. distillationwas distilled under reduced pressure
  7. customto remove t-butanol and toluene

Sources & evidence

ORD record
ord-c7692b406fbb43b39eaa216e458f101d
Source dataset
uspto-grants-2014_06
Patent number
US08741927B2

Reaction notes

Loading…