Sodium Hydroxide → N-(1-Methoxycarbonyl-3-methylthiopropyl)-alanyl-L-proline

HRID 1758839Notes

Reaction equation

HRID 1758839 reaction equation
[C:1]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])(=[O:5])[C:2]([CH3:4])=O.[CH3:14][O:15][C:16](=[O:23])[C@H:17]([CH2:19][CH2:20][S:21][CH3:22])[NH2:18].C([BH3-])#N.[Na+].[OH-].[Na+]>CO>[CH3:14][O:15][C:16]([CH:17]([NH:18][C@H:2]([C:1]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:4])[CH2:19][CH2:20][S:21][CH3:22])=[O:23]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 64684methyl (2S)-2-amino-4-(methylsulfanyl)butanoateHCID 5003444Sodium cyanoborohydrideHCID 10130260(S)-1-(2-Oxopropanoyl)pyrrolidine-2-carboxylic acid

Product 1

HCID 54124052N-(1-Methoxycarbonyl-3-methylthiopropyl)-alanyl-L-prolineYield 24.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of pyruvoyl-L-proline (185 mg), L-methionine methyl ester (600 mg), and sodium cyanoborohydride (200 mg) in 20 ml of methanol is adjusted to neutrality with dilute methanolic sodium hydroxide. After standing at room temperature for three days the product is absorbed on strong acid ion-exchange resin and eluted with 2% pyridine in water to yield 80 mg of product. The nmr spectrum shows OCH3 at 3.95δ, S-CH3 at 2.2δ and CH-CH3 at 1.55 and 1.7δ. The mass spectrogram on silylated material shows the expected molecular ion at 404 m/e.

Workup

  1. customthe product is absorbed on strong acid ion-exchange resin
  2. washeluted with 2% pyridine in water

Sources & evidence

ORD record
ord-41fed003f8bd48e69b4b0c7a9e269734
Source dataset
uspto-grants-1983_02
Patent number
US04374829

Reaction notes

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