4-Methylmorpholine → HCID 131718772, compound

HRID 2379418Notes

Reaction equation

HRID 2379418 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:15])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[NH2:7])[CH3:3].CN1CCOCC1.[C:23]1(=[O:42])[N:27]([C@@H:28]([CH2:32][CH2:33][CH2:34][CH2:35][OH:36])[C:29](O)=[O:30])[C:26](=[O:37])[C:25]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:24]12.OC1C2N=NNC=2C=CC=1.C(N=C=NCCCN(C)C)C>CN(C)C=O>[C:26]1(=[O:37])[N:27]([CH:28]([CH2:32][CH2:33][CH2:34][CH2:35][OH:36])[C:29]([NH:7][C@@H:6]([C:5]([O:4][CH2:2][CH3:3])=[O:15])[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:30])[C:23](=[O:42])[C:24]2=[CH:41][CH:40]=[CH:39][CH:38]=[C:25]12

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 165085Ethyl L-phenylalaninate hydrochlorideHCID 11065730(S)-2-Phthalimido-6-hydroxyhexanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 131718772HCID 131718772, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of L-phenylalanine ethyl ester hydrochloride salt (998 mg., 4.3 mmol) in dimethylformamide (10 mL.) was added with 4-methylmorpholine (575 μl, 529 mg., 5.2 mmol.). After stirring at room temperature for 5 minutes, the solution was cooled to 0° C. and treated successively with (S)-2-phthalimido-6-hydroxyhexanoic acid (1.002 g., 3.6 mmol.), hydroxybenzotriazole (582 mg., 4.3 mmol.) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (770 mg., 4.0 mmol.). The resulting mixture was stirred at 0° C. for 0.5 hour and at room temperature for 1.5 hours. The solution was partitioned between ethyl acetate and water and the organic extract was washed successively with 0.5N hydrochloric acid, water, 50% saturated sodium bicarbonate, and brine, then dried (sodium sulfate), filtered and stripped to give 1.63 g. of essentially pure title product as an oil/foam. TLC (1:1--acetone:hexanes) Rf =0.30.

Workup

  1. temperaturethe solution was cooled to 0° C.
  2. stirringThe resulting mixture was stirred at 0° C. for 0.5 hour and at room temperature for 1.5 hours
  3. customThe solution was partitioned between ethyl acetate and water
  4. extractionthe organic extract
  5. washwas washed successively with 0.5N hydrochloric acid, water, 50% saturated sodium bicarbonate, and brine
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. customto give 1.63 g

Sources & evidence

ORD record
ord-28333166bdac490db22b0ef28c651874
Source dataset
uspto-grants-1994_11
Patent number
US05362727

Reaction notes

Loading…