Water → HCID 19789839, compound

HRID 1351141Notes

Reaction equation

HRID 1351141 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11](=[O:14])[CH2:12][NH2:13].[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[C:25](Cl)=[O:26].O>ClCCl>[CH3:9][O:10][C:11](=[O:14])[CH2:12][NH:13][C:25]([C:16]1[CH:17]=[CH:18][C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:15]=1)=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 752462-Naphthoyl chlorideHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 19789839HCID 19789839, compoundYield 9,560.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2 °C

Procedure

Dichloromethane (66 mL) and then triethylamine (14.6 mL, 105 mmol, 2.0 eq.) were added to glycine methyl ester hydrochloride (6.61 g, 52.5 mmol, 1.0 eq.). A white precipitate appeared on the addition of the triethylamine, and the solution became a lot thicker. The mixture was stirred and cooled to 2° C. using an ice/water bath. A solution of 2-naphthoyl chloride (10.07 g, 52.5 mmol, 1.0 eq.) in dichloromethane (33 mL) was added over 15 minutes. The pale brown mixture was stirred for 25 hours at 5° C. Water (100 mL) was added and the mixture was stirred rapidly for 30 minutes at room temperature. The layers were separated. The organic layer was washed with sodium hydroxide (1 M, 100 mL) and then evaporated to dryness using a rotary evaporator to give an off-white solid (1221 g, 96%).

Workup

  1. stirringThe pale brown mixture was stirred for 25 hours at 5° C
  2. stirringthe mixture was stirred rapidly for 30 minutes at room temperature
  3. customThe layers were separated
  4. washThe organic layer was washed with sodium hydroxide (1 M, 100 mL)
  5. customevaporated to dryness
  6. customa rotary evaporator

Sources & evidence

ORD record
ord-22781d1996ae402698e5c2bc4b6d4d56
Source dataset
uspto-grants-2007_05
Patent number
US07217708B2

Reaction notes

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