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

HRID 1192

반응식

HRID 1192 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-64ae065485524aae852fadf8328767e1
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723457

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