4-Methyl-2-oxovaleric acid → HCID 54544378, compound

HRID 1758856Notes

Reaction equation

HRID 1758856 reaction equation
[Na].[CH3:2][CH:3]([CH3:10])[CH2:4][C:5](=O)[C:6]([OH:8])=[O:7].[NH2:11][C@H:12]([C:14]([NH:16][C@H:17]([C:28]([OH:30])=[O:29])[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)=[O:15])[CH3:13].C([BH3-])#N.[Na+]>O>[C:6]([CH:5]([NH:11][C@H:12]([C:14]([NH:16][C@H:17]([C:28]([OH:30])=[O:29])[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)=[O:15])[CH3:13])[CH2:4][CH:3]([CH3:10])[CH3:2])([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 704-Methyl-2-oxovaleric acidHCID 85362L-Alanyl-L-tryptophanHCID 5003444Sodium cyanoborohydrideHCID 5360545Sodium

Product 1

HCID 54544378HCID 54544378, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the sodium salt of 4-methyl-2-oxopentanoic acid (414 mg) and L-alanyl-L-tryptophan (150 mg) in water are adjusted to pH 7 with caustic and treated with sodium cyanoborohydride (103 mg) at room temperature for several days. The product is adsorbed on strong acid ion exchange resin and eluted with 2% pyridine in water. The product rich cuts are freeze dried affording 189 mg of fluffly white solid. The mass spectrum shows a molecular ion at 389 m/e and peaks at 187 m/e and 158 m/e for the fragments shown respectively: ##STR16## The nmr spectrum in D2O is consistent with structure.

Workup

  1. washeluted with 2% pyridine in water
  2. customdried
  3. customaffording 189 mg of fluffly white solid

Sources & evidence

ORD record
ord-8b6dc15b751d41289119cdf3d88019a1
Source dataset
uspto-grants-1983_02
Patent number
US04374829

Reaction notes

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