Hydrochloric Acid → Z-Phe-pro-OH

HRID 1197218노트

반응식

HRID 1197218 반응식
COS([O-])(=O)=O.C[S+](C)C1C=CC(O[C:16](=[O:36])[C@H:17]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[NH:18][C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])=CC=1.[NH:38]1[CH2:45][CH2:44][CH2:43][C@H:39]1[C:40]([OH:42])=[O:41].C(N(CC)CC)C.Cl>O>[CH2:22]([O:21][C:19]([NH:18][C@H:17]([C:16]([N:38]1[CH2:45][CH2:44][CH2:43][C@H:39]1[C:40]([OH:42])=[O:41])=[O:36])[CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:20])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 145742L-ProlineHCID 88483144Benzyloxycarbonylphenylalanine p-dimethylsulfoniophenyl ester methylsulfate

생성물 1

HCID 11899094Z-Phe-pro-OH

시약·촉매·용매 1

HCID 962Water용매

실험 절차

In 30 ml of water was dissolved 5.47 g of benzyloxycarbonylphenylalanine p-dimethylsulfoniophenyl ester methylsulfate obtained by a synthesizing method according to Synthetic Example 5, and 20 ml of an aqueous solution of 1.15 g of proline and 1.4 ml of triethylamine was dropwise added thereto under stirring. The reaction mixture was further stirred for 12 hours at room temperature, adjusted to pH 2 by adding 2% HCl, and extracted twice with 50 ml of ethyl acetate. The ethyl acetate layer was washed with water, dried, and concentrated under reduced pressure, and the obtained residue was recrystallized by adding ether. This crystalline product indicated only the peak of the desired product by HPLC.

후처리

  1. customobtained by a synthesizing method
  2. additionwas dropwise added
  3. stirringThe reaction mixture was further stirred for 12 hours at room temperature
  4. extractionextracted twice with 50 ml of ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customthe obtained residue was recrystallized
  9. additionby adding ether

출처 및 근거

ORD 기록
ord-6fe191b3557b436c8ff41d68c2cabeb2
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05117031

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