4-Methylmorpholine → (S)-N-(2-Phthalimido-1-oxohexyl)glycine, ethyl ester

HRID 1326

Reaction equation

HRID 1326 reaction equation
Cl.[NH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].CN1CCOCC1.[C:16]1(=[O:35])[N:20]([C@@H:21]([CH2:25][CH2:26][CH2:27][CH2:28]O)[C:22](O)=[O:23])[C:19](=[O:30])[C:18]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:17]12.OC1C2N=NNC=2C=CC=1>CN(C)C=O>[C:19]1(=[O:30])[N:20]([C@@H:21]([CH2:25][CH2:26][CH2:27][CH3:28])[C:22]([NH:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:23])[C:16](=[O:35])[C:17]2=[CH:34][CH:33]=[CH:32][CH:31]=[C:18]12

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 11065730(S)-2-Phthalimido-6-hydroxyhexanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 131719537(S)-N-(2-Phthalimido-1-oxohexyl)glycine, ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A slurry of glycine, ethyl ester, hydrochloride salt (2.718 g, 19.5 mmol.) in dimethylformamide (36 ml.) was treated with 4-methyl morpholine (2.60 ml., 2.39 g., 23.6 mmol.) and stirred at room temperature for 5 minutes. The mixture was then treated with (S)-2-phthalimido-6-hydroxyhexanoic acid (4.50 g., 16.2 mmol.) and hydroxybenzotriazole (2.225 g., 16.5 mmol.), cooled to 0° C., and then treated with ethyl-3-(3-dimethylamino)propyl carbodiimide, hydrochloride salt (3.438 g., 17.9 mmol.). After stirring at 0° C. for 1 hour and at room temperature for 2 hours, the mixture was partitioned between ethyl acetate and 0.5N hydrochloric acid and subsequently extracted three times with ethyl acetate. The pooled ethyl acetate extracts were washed in succession with water, saturated sodium bicarbonate, and brine, then dried (sodium sulfate), filtered and stripped to give 5.77 g. of title product as a colorless oil. TLC (ethyl acetate) Rf =0.34.

Workup

  1. temperaturecooled to 0° C.
  2. stirringAfter stirring at 0° C. for 1 hour and at room temperature for 2 hours
  3. customthe mixture was partitioned between ethyl acetate and 0.5N hydrochloric acid
  4. extractionsubsequently extracted three times with ethyl acetate
  5. washThe pooled ethyl acetate extracts were washed in succession with water, saturated sodium bicarbonate, and brine
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. customto give 5.77 g

Sources & evidence

ORD record
ord-32b402f60fe74c78b310c537e44ff646
Source dataset
uspto-grants-1998_03
Patent number
US05723602

Linked notes

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