Calcium Acetate → N-benzyloxycarbonyl (beta-benzyl)-L-aspartyl-L-phenylalanine methyl ester

HRID 1111842Notes

Reaction equation

HRID 1111842 reaction equation
C([O-])(=O)C.[Ca+2].C([O-])(=O)C.[CH2:10]([O:17][C:18]([NH:20][CH:21]([C:33](O)=[O:34])[CH:22]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:23]([OH:25])=[O:24])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:36][O:37][C:38](=[O:48])[C@H:39]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[NH2:40].[OH-].[Na+]>CN(C)C=O>[CH3:36][O:37][C:38](=[O:48])[C@H:39]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[NH:40][C:33](=[O:34])[C@H:21]([CH:22]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:23](=[O:24])[OH:25])[NH:20][C:18]([O:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:19]

Participants

6

Reactant 4

HCID 6116Calcium AcetateHCID 14798Sodium HydroxideHCID 736234L-Phenylalanine, methyl esterHCID 18324139N-benzyloxycarbonyl-(beta-benzyl)-D,L-aspartic acid

Product 1

HCID 14876780N-benzyloxycarbonyl (beta-benzyl)-L-aspartyl-L-phenylalanine methyl esterYield 79.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
30 °C

Procedure

A 100 mg amount of Thermoase and 100 mg of an inhibitor for proteolytic enzyme obtained from the potato were admixed with 10 ml of tris-hydrochloric acid buffer solution (pH 8.0) containing 2.0 × 10-2M of calcium acetate. The mixture was stirred at 30° C. for 10 minutes. The insoluble material was removed by filtering the solution through a glass filter (G-3). The filtrate was mixed with 715 mg (2.00 mmol) of N-benzyloxycarbonyl-(β-benzyl)-D,L-aspartic acid and 215 mg (1.00 mmol) of L-phenylalanine methyl ester and then 1N NaOH was added to the filtrate to adjust the pH to 7.5. The reaction was carried out with stirring at 39° C. for 17 hours. The resulting white precipitate was treated in accordance with the process of Example 1 whereby 411 mg (yield of 79.2%) of N-benzyloxycarbonyl-(β-benzyl)-L-aspartyl-L-phenylalanine methyl ester having an [α]D23 = -12.5 (C=1.0 dimethylformamide)

Workup

  1. customA 100 mg amount of Thermoase and 100 mg of an inhibitor for proteolytic enzyme obtained from the potato
  2. customThe insoluble material was removed
  3. filtrationby filtering the solution through a glass
  4. filtrationfilter (G-3)
  5. stirringwith stirring at 39° C. for 17 hours

Sources & evidence

ORD record
ord-554eda8bc5b542fe905b0a2b250d8169
Source dataset
uspto-grants-1978_10
Patent number
US04119493

Reaction notes

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