Hydrochloric Acid → Z-Phe-pro-OH

HRID 1197218Notes

Reaction equation

HRID 1197218 reaction equation
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

Participants

6

Reactant 4

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

Product 1

HCID 11899094Z-Phe-pro-OH

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6fe191b3557b436c8ff41d68c2cabeb2
Source dataset
uspto-grants-1992_05
Patent number
US05117031

Reaction notes

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