4-Methylmorpholine → (+/-)-N-Formyl-(4-chlorophenyl)alanine methyl ester

HRID 546495Notes

Reaction equation

HRID 546495 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:15])[C@H:5]([CH3:14])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.CN1CC[O:43][CH2:42]C1>ClCCl.C(O)=O>[CH3:2][O:3][C:4](=[O:15])[C@H:5]([CH3:14])[N:6]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)[CH:42]=[O:43]

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 18442857(+/-)-N-Formyl-(4-chlorophenyl)alanine methyl ester

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

(±)-(4-Chlorophenyl)alanine methyl ester hydrochloride (2.00 g) was suspended in dichloromethane (20 ml), and 3-(3-dimethylaminopropyl)-1-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 dichloromethane. After an organic 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 (dichloromethane:methanol=40:1) to obtain the title compound (1.21 g) as a yellow oil.

Workup

  1. stirringto stir the mixture for 15 minutes
  2. washAfter an organic 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 (dichloromethane:methanol=40:1)

Sources & evidence

ORD record
ord-dc5467e7a6c7489b9164ad1deb780bba
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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