Potassium Carbonate → Nalpha-benzyloxycarbonyl-L-histidyl-L-proline benzyl ester

HRID 64816

반응식

HRID 64816 반응식
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:19]([NH:21]N)=[O:20])[CH2:13][C:14]1[N:18]=[CH:17][NH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+].[CH2:33]([O:40][C:41](=[O:47])[C@@H:42]1[CH2:46][CH2:45][CH2:44]N1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>Cl.C(OCC)(=O)C>[CH2:33]([O:40][C:41](=[O:47])[C@@H:42]1[CH2:46][CH2:45][CH2:44][N:21]1[C:19](=[O:20])[C@H:12]([CH2:13][C:14]1[N:18]=[CH:17][NH:16][CH:15]=1)[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 736155Benzyl L-prolinateHCID 23668193Sodium NitriteHCID 178514453HCID 178514453, 화합물

생성물 1

HCID 178523868Nalpha-benzyloxycarbonyl-L-histidyl-L-proline benzyl ester수율 49.9%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 8857Ethyl Acetate용매2회

실험 절차

In 99 ml of an aqueous solution of 1N hydrochloric acid was dissolved 10.01 g of Nα -benzyloxycarbonyl-L-histidine hydrazide (3). After adding thereto 132 ml of ethyl acetate, 8.25 ml of an aqueous solution of 2.313 g of sodium nitrite was added to the mixture with stirring vigorously under ice-cooling. After performing the reaction at 0° C. for 5 minutes, 39.6 ml of an aqueous 50% potassium carbonate solution was added to the reaction mixture under ice-cooling to alkalify the solution. The reaction mixture was placed in a separation funnel and an organic layer thus formed was collected. Furthermore, the aqueous layer was extracted by 20 ml of ethyl acetate and the extract was combined with the foregoing organic layer. The mixture was dried over anhydrous sodium sulfte under ice-cooling for 10 minutes. By removing anhydrous sodium sulfate by filtration, 152 ml of an ethyl acetate solution of Nα -benzyloxycarbonyl-L-histidine azide (4) was obtained. The product was ice-cooled and 20 ml of an ethyl acetate solution of 5.703 g of L-proline benzyl ester (5) was added thereto. The mixture was reacted overnight at 0° C. and then the reaction mixture was concentrated to dryness. The residue was dissolved in 22 ml of chloroform-methanol (10:1) and subjected to silica gel column chromatography. The eluate by chloroform-methanol (95:5) was concentrated to dryness to provide 6.602 g of Nα -benzyloxycarbonyl-L-histidyl-L-proline benzyl ester (6).

후처리

  1. additionAfter adding
  2. temperaturecooling
  3. customthe reaction at 0° C. for 5 minutes
  4. temperaturecooling
  5. customThe reaction mixture was placed in a separation funnel
  6. customan organic layer thus formed
  7. customwas collected
  8. extractionFurthermore, the aqueous layer was extracted by 20 ml of ethyl acetate
  9. dry with materialThe mixture was dried over anhydrous sodium sulfte under ice-
  10. temperaturecooling for 10 minutes
  11. customBy removing anhydrous sodium sulfate
  12. filtrationby filtration, 152 ml of an ethyl acetate solution of Nα -benzyloxycarbonyl-L-histidine azide (4)
  13. customwas obtained
  14. temperaturecooled
  15. customThe mixture was reacted overnight at 0° C.
  16. concentrationthe reaction mixture was concentrated to dryness
  17. dissolutionThe residue was dissolved in 22 ml of chloroform-methanol (10:1)
  18. concentrationThe eluate by chloroform-methanol (95:5) was concentrated to dryness

출처 및 근거

ORD 기록
ord-a14d5e29deb644788fe00c08f3c75ae6
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04610821

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