Triethylamine → HCID 21958029, compound

HRID 2299209Notes

Reaction equation

HRID 2299209 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][C:13]=1[Cl:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([NH:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:18])=[CH:14][C:13]=1[Cl:21])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 151417Glycine tert-butyl esterHCID 21958048HCID 21958048, compound

Product 1

HCID 21958029HCID 21958029, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Benzyloxycarbonylamino-3-chlorobenzoic acid (0.80 g) was dissolved in N,N-dimethylformamide (24.0 ml) and admixed at room temperature with t-butyl glycinate (0.44 g) and triethylamine (0.77 ml). Diethyl cyanophosphate (0.43 ml) was added with ice-cooling, and the mixture was stirred under a nitrogen atmosphere at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was separated and the aqueous layer was extracted with ethyl acetate. The ethyl acetate layers were combined and washed three times with water and then twice with saturated brine, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was crystallized from a mixture of ethyl acetate and diisopropyl ether to yield t-butyl N-(4-benzyloxycarbonylamino-3-chlorobenzoyl)glycinate (0.93 g) as white crystals.

Workup

  1. temperaturecooling
  2. washwashed with water
  3. customThe ethyl acetate layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washwashed three times with water
  6. dry with materialtwice with saturated brine, and then dried over magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was crystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-62a48cc6985e408dbcd97578415d2648
Source dataset
uspto-grants-2002_12
Patent number
US06495604B1

Reaction notes

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