Isobutylamine → HCID 86602883, compound

HRID 852631Notes

Reaction equation

HRID 852631 reaction equation
CO[C:3](=[O:18])[C@@H:4]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@H:5]([OH:9])[CH2:6][CH2:7][CH3:8].[CH2:19]([NH2:23])[CH:20]([CH3:22])[CH3:21]>>[C:14]([O:13][C:11](=[O:12])[NH:10][C@H:4]([C:3](=[O:18])[NH:23][CH2:19][CH:20]([CH3:22])[CH3:21])[C@H:5]([OH:9])[CH2:6][CH2:7][CH3:8])([CH3:15])([CH3:16])[CH3:17]

Participants

3

Reactant 2

HCID 6558IsobutylamineHCID 86602884HCID 86602884, compound

Product 1

HCID 86602883HCID 86602883, compoundYield 84%

Procedure

(2S,3R)-2-tert-Butoxycarbonylamino-3-hydroxy-hexanoic acid methyl ester (D94) (1.57 g, 6.02 mmol, 1 equiv) was refluxed in iso-butylamine (10 ml) for 2 h. The solution was concentrated in vacuo and the residue purified by flash chromatography on silica gel to give ((1S,2R)-2-hydroxy-1-isobutylcarbamoyl-pentyl)-carbamic acid tert-butyl ester (G33) (1.52 g, 84%) as a white solid.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-433ae12f1e844d0b8066a69f6bdb9f84
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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