Pyridine → HCID 59865135, compound

HRID 2244430Notes

Reaction equation

HRID 2244430 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH:5]([NH2:8])[C:6]#[N:7])[CH3:2].N1C=CC=CC=1.[CH3:16][O:17][CH2:18][C:19](Cl)=[O:20]>ClCCl>[CH2:1]([O:3][C:4](=[O:9])[CH:5]([C:6]#[N:7])[NH:8][C:19](=[O:20])[CH2:18][O:17][CH3:16])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 96623Methoxyacetyl chlorideHCID 288716Ethyl 2-amino-2-cyanoacetate

Product 1

HCID 59865135HCID 59865135, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of aminocyanacetic acid ethyl ester (1.00 g, 7.80 mmol) in dichloromethane (15.00 ml) was cooled to 0° C. and treated with pyridine (0.62 g, 7.80 mmol). Methoxy-acetyl chloride (0.85 g, 7.80 mmol) was added dropwise during 15 min. The mixture was stirred for 5 min at 0° C., then warmed to room temperature and stirred for 10 min. The volatiles were evaporated, and the residue was redissolved in dichloromethane and washed twice with water. The organic layer was dried with sodium sulphate and evaporated. The residue was triturated in diisopropyl ether to yield cyano-(2-methoxy-acetylamino)-acetic acid ethyl ester (1.04 g, 66%), MS (ISP): m/e=201.1 (M+H+).

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 10 min
  3. customThe volatiles were evaporated
  4. dissolutionthe residue was redissolved in dichloromethane
  5. washwashed twice with water
  6. dry with materialThe organic layer was dried with sodium sulphate
  7. customevaporated
  8. customThe residue was triturated in diisopropyl ether

Sources & evidence

ORD record
ord-f7120c5a5f5b40eab7532e15171af6af
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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