N-甲基吗啉 → (S)-N-(2-Phthalimido-1-oxohexyl)glycine, ethyl ester

HRID 1326

反应方程式

HRID 1326 反应方程式
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

参与物

6

反应物 4

HCID 7972N-甲基吗啉HCID 2723640甘氨酸乙酯盐酸盐HCID 11065730(S)-2-Phthalimido-6-hydroxyhexanoic acidHCID 178418300HCID 178418300，化合物

产物 1

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

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-32b402f60fe74c78b310c537e44ff646
来源数据集
uspto-grants-1998_03
专利号
US05723602

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