(2S)-2-[[(2S)-1-ethoxy-1-oxopentan-2-yl]amino]propanoic acid → HCID 53755056, compound

HRID 1886329Notes

Reaction equation

HRID 1886329 reaction equation
[C:1]([C@@H:4]1[CH:9]2[CH2:10][CH2:11][CH:6]([CH2:7][CH2:8]2)[NH:5]1)(=[O:3])[NH2:2].[CH2:12]([O:14][C:15]([C@@H:17]([NH:21][C@H:22]([C:24](O)=[O:25])[CH3:23])[CH2:18][CH2:19][CH3:20])=[O:16])[CH3:13]>>[CH2:12]([O:14][C:15]([C@@H:17]([NH:21][C@@H:22]([CH3:23])[C:24]([N:5]1[C@H:4]([C:1](=[O:3])[NH2:2])[CH:9]2[CH2:10][CH2:11][CH:6]1[CH2:7][CH2:8]2)=[O:25])[CH2:18][CH2:19][CH3:20])=[O:16])[CH3:13]

Participants

3

Reactant 2

HCID 10015159(2S)-2-[[(2S)-1-ethoxy-1-oxopentan-2-yl]amino]propanoic acidHCID 45084389HCID 45084389, compound

Product 1

HCID 53755056HCID 53755056, compoundYield 58%

Procedure

Using the (DCC/HOBT) peptide coupling method described by W. KONIG and R. GEIGER (Ber, 103, 788, 1970) the expected product is prepared from 0.02 mol of (3S)-3-carbamoyl-2-azabicyclo[2.2.2]octane, described in Patent FR 2,585,709, and 0.02 mol of (S)-N-[(S)-1-(ethoxycarbonyl)butyl]alanine, described by VINCENT et al (Tetrahedron Letters 23, (1982), 1677-1680), the product being purified by chromatography on silica gel (elution solvent: dichloromethane/ethanol, 90:10) and then lyophilized.

Workup

  1. customthe product being purified by chromatography on silica gel (elution solvent: dichloromethane/ethanol, 90:10)

Sources & evidence

ORD record
ord-97af9cf98e314d878a5d58f4a22ad5f0
Source dataset
uspto-grants-1992_09
Patent number
US05151432

Reaction notes

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