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

HRID 459548Notes

Reaction equation

HRID 459548 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 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 (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 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 (dichloromethane methanol=40:1)

Sources & evidence

ORD record
ord-fffbb675ff4741c2b38d89a74b5f3c11
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

Loading…