Hydrochloric Acid → HCID 14802668, 화합물

HRID 65598노트

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HRID 65598 반응식
Cl.N(OCCC(C)C)=O.[CH2:10]([O:17][C:18]([NH:20][C@H:21]([C:24]([NH:26][C@H:27]([C:36]([N:38]=[N+]=[N-])=[O:37])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)=[O:25])[CH2:22][OH:23])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.[CH3:42][O:43][C:44](=[O:55])[C@H:45]([CH2:51][CH:52]([CH3:54])[CH3:53])[NH:46][C:47](=[O:50])[CH2:48]N>O1CCCC1.C(N(CC)CC)C.CN(C)C=O>[CH3:42][O:43][C:44](=[O:55])[C@H:45]([CH2:51][CH:52]([CH3:53])[CH3:54])[NH:46][C:47](=[O:50])[CH2:48][NH:38][C:36](=[O:37])[C@H:27]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)[NH:26][C:24](=[O:25])[C@H:21]([CH2:22][OH:23])[NH:20][C:18]([O:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:19]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 13751932methyl (2S)-2-(2-aminoacetamido)-4-methylpentanoate hydrochlorideHCID 54294707N-benzyloxycarbonyl-L-seryl-L-tyrosyl azide

생성물 1

HCID 14802668HCID 14802668, 화합물

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매2회

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온도
-60 °C

실험 절차

To a stirred solution of 7.49 g. of N-benzyloxycarbonyl-L-seryl-L-tyrosyl hydrazide [this compound is reported in Helv. Chim. Acta, 41, 1852 (1958)] in 50 ml. of N,N-dimethylformamide, cooled to -30° C., is first added 16.9 ml. of 3.607 N hydrogen chloride in tetrahydrofuran and then 2.7 ml. of isoamyl nitrite, and the resulting mixture is stirred at -30° C. for 30 minutes. The mixture, which contains N-benzyloxycarbonyl-L-seryl-L-tyrosyl azide, is next cooled to -60° C., and to it are added first 8.57 ml. of triethylamine, then 4.297 g. of glycyl-L-leucine methyl ester hydrochloride and finally 2.52 ml. more of triethylamine. The stirred mixture is allowed to warm to 0° C. during one hour and is stirred at 0° C. for one hour and kept at -5° C. for 48 hours. It is then filtered, and the filtrate is evaporated under reduced pressure at 40°-50° C. The gummy residue is partitioned between dilute hydrochloric acid and ethyl acetate, and the organic layer is separated, washed with saturated aqueous sodium bicarbonate and with saturated aqueous sodium chloride, dried, and evaporated to give a solid residue of N-benzyloxycarbonyl-L-seryl-L-tyrosylglycyl-L-leucine methyl ester; m.p. 166°-167° C., following two crystallizations from ethyl acetate-ether; [α]D25 -25.4° (2% in N,N-dimethylformamide); [α]D25 -38.2° (2.09% in methanol).

후처리

  1. additionto it are added first 8.57 ml
  2. temperatureto warm to 0° C. during one hour
  3. waitkept at -5° C. for 48 hours
  4. filtrationIt is then filtered
  5. customthe filtrate is evaporated under reduced pressure at 40°-50° C
  6. customThe gummy residue is partitioned between dilute hydrochloric acid and ethyl acetate
  7. customthe organic layer is separated
  8. washwashed with saturated aqueous sodium bicarbonate and with saturated aqueous sodium chloride
  9. customdried
  10. customevaporated

출처 및 근거

ORD 기록
ord-5f8374911abc4e3eb30bcfdb09930e6c
출처 데이터셋
uspto-grants-1978_12
특허 번호
US04128540

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