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

HRID 2104350Notes

Reaction equation

HRID 2104350 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>[CH3:2][O:3][C:4](=[O:15])[CH:5]([NH:6][CH:7]=[O:28])[CH2:14][C:33]1[CH:38]=[CH:37][C:36]([Cl:1])=[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 to the suspension were added 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), followed by stirring for 15 minutes. Subsequently, formic acid (0.30 mL) addition and subsequent stirring for 15 minutes were repeated 3 times. The reaction mixture was diluted with methylene chloride. The organic layer was washed with water, and was dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride:methanol=40:1), to thereby give the title compound (1.21 g).

Workup

  1. stirringsubsequent stirring for 15 minutes
  2. washThe organic layer was washed with water
  3. dry with materialwas dried over sodium sulfate anhydrate
  4. distillationThe solvent was distilled away under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (methylene chloride:methanol=40:1)

Sources & evidence

ORD record
ord-4cc993f48e9141c29de111ce86409f22
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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