Hydrochloric Acid → Z-Phe-pro-OH

HRID 1586895ノート

反応式

HRID 1586895 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 11899094Z-Phe-pro-OH

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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 added dropwise thereto while 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 resultant residue was recrystallized by adding ether. This crystalline product indicated only the peak of the desired product by HPLC.

後処理

  1. customobtained by a synthesizing method
  2. additionwas added dropwise
  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 resultant residue was recrystallized
  9. additionby adding ether

出典と根拠

ORDレコード
ord-e849fa4701b14f40af4d263230869086
出典データセット
uspto-grants-1993_06
特許番号
US05216125

反応ノート

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