Hydrochloric Acid → Z-D-Pro-Val-MeVal-Pro-Pro-NHBn

HRID 989607Notes

Reaction equation

HRID 989607 reaction equation
[NH:1]1[CH2:44][CH2:43][CH2:42][C@@H:2]1[C:3]([NH:5][C@H:6]([C:10]([N:12]([CH3:41])[C@H:13]([C:17]([N:19]1[CH2:40][CH2:39][CH2:38][C@H:20]1[C:21]([N:23]1[CH2:37][CH2:36][CH2:35][C@H:24]1[C:25]([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[O:22])=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])[CH:7]([CH3:9])[CH3:8])=[O:4].Cl.[CH2:46]=[O:47].[CH3:48][OH:49]>[Pd].C>[N:1]1([C:46]([O:49][CH2:48][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:47])[CH2:44][CH2:43][CH2:42][C@@H:2]1[C:3]([NH:5][C@H:6]([C:10]([N:12]([CH3:41])[C@H:13]([C:17]([N:19]1[CH2:40][CH2:39][CH2:38][C@H:20]1[C:21]([N:23]1[CH2:37][CH2:36][CH2:35][C@H:24]1[C:25]([NH:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])=[O:22])=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])[CH:7]([CH3:9])[CH3:8])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 887MethanolHCID 15513124HCID 15513124, compound

Product 1

HCID 131722144Z-D-Pro-Val-MeVal-Pro-Pro-NHBn

Reagents, catalysts & solvents 1

HCID 14818447PalladiumcarbonCatalyst

Procedure

1.94 g (3 mmol) of D-Pro-Val-MeVal-Pro-Pro-NHBn×HCl was dissolved in 30 ml methanol. To this solution was then added 0.3 g 10% Pd/charcoal and 1.5 ml aqueous formaldehyde solution and the reaction mixture was hydrogenated. Following filtration and evaporation of the solvents, the resulting residue was dissolved in water, adjusted to pH 2 and extracted twice with diethyl ether and several additional times with dichloromethane. The aqueous phase was adjusted to pH 9-10 and extracted twice with dichloromethane. The organic extracts were dried over sodium sulfate and evaporated to dryness. The residue was crystallized as the hydrochloride salt to give 0.5 g of the desired product which was characterized by fast atom bombardment mass spectrometry ([M+H]+=625).

Workup

  1. filtrationfiltration and evaporation of the solvents
  2. dissolutionthe resulting residue was dissolved in water
  3. extractionextracted twice with diethyl ether and several additional times with dichloromethane
  4. extractionextracted twice with dichloromethane
  5. dry with materialThe organic extracts were dried over sodium sulfate
  6. customevaporated to dryness
  7. customThe residue was crystallized as the hydrochloride salt

Sources & evidence

ORD record
ord-036a5a11f1374c989cb57b3542191c97
Source dataset
uspto-grants-2002_10
Patent number
US06458765B1

Reaction notes

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