4-Methylmorpholine → Methyl 3-(4-chlorophenyl)-2-formamidopropanoate

HRID 902835Notes

Reaction equation

HRID 902835 reaction equation
[ClH:1].[CH3:2][O:3][C:4](=[O:15])[C@H:5]([CH3:14])[NH:6][C:7]1C=CC(Cl)=CC=1.Cl.CN(C)CCCN=C=NCC.[OH2:28].ON1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2N=N1.CN1CCOCC1>C(Cl)Cl.C(O)=O>[Cl:1][C:33]1[CH:38]=[CH:37][C:36]([CH2:14][CH:5]([NH:6][CH:7]=[O:28])[C:4]([O:3][CH3:2])=[O:15])=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67056399(+/-)-(4-Chlorophenyl)alanine methyl ester hydrochloride

Product 1

HCID 14318072Methyl 3-(4-chlorophenyl)-2-formamidopropanoateYield 62.6%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

(±)-(4-Chlorophenyl)alanine methyl ester hydrochloride (2.00 g) was suspended in methylene chloride (20 ml), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.60 g), 1-hydroxybenzotriazole monohydrate (1.23 g), N-methylmorpholine (1.90 ml) and formic acid (0.30 ml) were added to stir the mixture for 15 minutes. After a process in which formic acid (0.30 ml) was additionally added to stir the mixture for 15 minutes was repeated 3 times, the reaction mixture was diluted with methylene chloride. After an ogranic layer was washed with water and then dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (methylene chloride:methanol=40:1) to obtain the title compound (1.21 g).

Workup

  1. stirringto stir the mixture for 15 minutes
  2. washAfter an ogranic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (methylene chloride:methanol=40:1)

Sources & evidence

ORD record
ord-aa83c700fa0e42fcab14e01fcf792750
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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