Dimethylformamide → HCID 86742709, compound

HRID 2292354Notes

Reaction equation

HRID 2292354 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=O)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)C=O.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[NH2:26]>ClCCl>[CH3:21][O:22][C:23]1[CH:24]=[C:25]([NH:26][C:13](=[O:15])[CH2:12][NH:11][C:9](=[O:10])[O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:27]=[CH:28][C:29]=1[O:30][CH3:31]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 14349BenzyloxycarbonylglycineHCID 227703,4-Dimethoxyaniline

Product 1

HCID 86742709HCID 86742709, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 25.9 g (124 mmol) of N-(phenylmethoxycarbonyl)glycine in 370 ml of dichloromethane, were added at 0° C., 0.74 ml of dimethylformamide and 18.8 g (148 mmol) of oxyalylchloride. The mixture was allowed to warm to room temperature and was then added dropwise to a mixture of 19.0 g (124 mmol) of 3,4-dimethoxyaniline (sublimed) and washed with 10% hydrochloric acid solution and twice with water, and dried over sodium sulfate. After the evaporation of the solvent, the residue was triturated with ether and dried in vacuo; yield: 26.3 g.

Workup

  1. additionwere added at 0° C.
  2. washwashed with 10% hydrochloric acid solution and twice with water
  3. dry with materialdried over sodium sulfate
  4. customAfter the evaporation of the solvent
  5. customthe residue was triturated with ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-fc5c9ad4604647ebb7e3c8a24ab57cae
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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