Hydrochloric Acid → HCID 131710410, compound

HRID 1282708Notes

Reaction equation

HRID 1282708 reaction equation
Cl.[NH2:2][C@H:3]([C:11]([O:13][CH3:14])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N:15]1([C:41]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:42])[CH2:40][CH2:39][CH2:38][C@H:16]1[C:17]([NH:19][C@H:20]([C:24]([NH:26][C@H:27]([C:35](O)=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:25])[CH:21]([CH3:23])[CH3:22])=[O:18].[OH-].[Na+]>C(O)(=O)CC(CC(O)=O)(C(O)=O)O.O>[N:15]1([C:41]([O:43][CH2:44][C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[O:42])[CH2:40][CH2:39][CH2:38][C@H:16]1[C:17]([NH:19][C@H:20]([C:24]([NH:26][C@H:27]([C:35]([NH:2][C@H:3]([C:11]([O:13][CH3:14])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:36])[CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:25])[CH:21]([CH3:23])[CH3:22])=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 736234L-Phenylalanine, methyl esterHCID 714437581-[(Benzyloxy)carbonyl]-L-prolyl-L-valyl-L-phenylalanine

Product 1

HCID 131710410HCID 131710410, compoundYield 37.2%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 962WaterSolvent

Procedure

A solution of 0.216 g (10 mmol) of HCl.H-Phe-OCH3 (MW 215.5) in 40 ml of citric acid buffer solution (pH = 4.0) was added to a solution of 0.495 g (10 mmol) of Z-Pro-Val-Phe-OH (MW 495) in 10 ml of 1N-NaOH, and 30 ml of water was further added with stirring. A 0.1 g sample of pepsin (1:10000) was added to the mixture with stirring at 40°C for 24 hours to react them. The resulting white precipitate was filtered by a glass filter (G-3) and was sequentially washed with 5% ammonia water, 5% citric acid aqueous solution and water. The product was dried above P2O5 under reduced pressure at 50°C to obtain 0.244 g of Z-Pro-Val-Phe-Phe-OCH3 having a melting point of 199°-201°C and [α]D30 = -33.2 (c = 1, DMF). The yield was 37.2%.

Workup

  1. additionwas further added
  2. additionA 0.1 g sample of pepsin (1:10000) was added to the mixture
  3. stirringwith stirring at 40°C for 24 hours
  4. customto react them
  5. filtrationThe resulting white precipitate was filtered by a glass
  6. filtrationfilter (G-3)
  7. washwas sequentially washed with 5% ammonia water, 5% citric acid aqueous solution and water
  8. dry with materialThe product was dried above P2O5 under reduced pressure at 50°C

Sources & evidence

ORD record
ord-994d80bea4e54307846f5fa56e6e04ab
Source dataset
uspto-grants-1976_08
Patent number
US03972773

Reaction notes

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