Hydrochloric Acid → HCID 131710411, compound

HRID 1282709Notes

Reaction equation

HRID 1282709 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.[NH:15]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:16][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.CN(C=O)C.O>[NH:15]([C:38]([O:40][C:41]([CH3:43])([CH3:42])[CH3:44])=[O:39])[CH2:16][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]([CH3:22])[CH3:23])=[O:18]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 736234L-Phenylalanine, methyl esterHCID 131710412HCID 131710412, compound

Product 1

HCID 131710411HCID 131710411, compoundYield 71.2%

Reagents, catalysts & solvents 3

HCID 311Citric AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

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 0.421 g of BOC-Gly-Val-Phe-OH (MW 421) in 10 ml of 1N-NaOH and 30 ml of water was further added with stirring. Then, 0.1 g of pepsin (1:10000) was added to the mixture with stirring in an incubator at 40°C for 24 hours to react them. 0.414 g of BOC-Gly-Val-Phe-Phe-OCH3 having a melting point of 193° - 196°C and [α]D30 = -14.8 (c = 1, DMF) was obtained. The yield was 71.2%.

Workup

  1. additionwas further added
  2. additionThen, 0.1 g of pepsin (1:10000) was added to the mixture
  3. stirringwith stirring in an incubator at 40°C for 24 hours
  4. customto react them

Sources & evidence

ORD record
ord-07edb088ae2e46c1b2d009bb136035f4
Source dataset
uspto-grants-1976_08
Patent number
US03972773

Reaction notes

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