N-Phenylglycine → HCID 86689288, compound

HRID 537305Notes

Reaction equation

HRID 537305 reaction equation
[C:1]1([NH:7][CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][C:14]=1[NH:22][CH2:23][CH:24]([CH3:26])[CH3:25]>C1COCC1>[CH2:20]([O:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:9](=[O:11])[CH2:8][NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:14]([NH:22][CH2:23][CH:24]([CH3:25])[CH3:26])[CH:15]=1)[CH3:21]

Participants

4

Reactant 2

HCID 66025N-PhenylglycineHCID 86689287HCID 86689287, compound

Product 1

HCID 86689288HCID 86689288, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of N-phenylglycine (1.51 g, 0.01 mol) and N,N′-carbonyldiimidazole (1.62 g, 0.01 mol) in THF (25 mL) was heated at 50° C. for 30 min under Ar. A solution of 55 (2.08 g, 0.01 mol) in THF (50 mL) was then added over 30 min, and the resulting mixture was heated at 70° C. overnight. The reaction mixture was concentrated in vacuo, and the residue was dissolved in EtOAc (100 mL) and washed with saturated NaHCO3 (2×100 mL) and brine (100 mL). The organic phase was filtered through phase separation filter paper and concentrated in vacuo to give 3.0 g of a red oil which was used in the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in EtOAc (100 mL)
  3. washwashed with saturated NaHCO3 (2×100 mL) and brine (100 mL)
  4. filtrationThe organic phase was filtered through phase separation
  5. filtrationfilter paper
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dc9ac579c031465aa1ee36bcfbd409c5
Source dataset
uspto-grants-2014_10
Patent number
US08859780B2

Reaction notes

Loading…