Diisopropylethylamine → HCID 54013482, compound

HRID 1732526Notes

Reaction equation

HRID 1732526 reaction equation
Cl.[C:2]([O:6][C:7](=[O:13])[C@H:8]([CH:10]([CH3:12])[CH3:11])[NH2:9])([CH3:5])([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.[N+](C1C=CC([O:32][C:33](=O)[C@H:34]([CH3:46])[NH:35][C:36]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:37])=CC=1)([O-])=O>CN(C=O)C>[C:2]([O:6][C:7](=[O:13])[C@H:8]([CH:10]([CH3:11])[CH3:12])[NH:9][C:33](=[O:32])[C@H:34]([CH3:46])[NH:35][C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 70218781168-87-2HCID 12490702tert-butyl (2S)-2-amino-3-methylbutanoate hydrochloride

Product 1

HCID 54013482HCID 54013482, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of L-valine tert-butyl ester hydrochloride (2.1 g, 10 mmole) in DMF (10 ml) was treated with DIEA (1.6 ml. 10 mmole) and benzyloxycarbonyl-L-alanine p-nitrophenyl ester (3.5 g, 10 mmole). After overnight at room temperature, the solution was filtered through a column of neutral Al2O3 (100 g) and eluted with DMF. The solvent was removed in vacuo and the residue filtered through a column of silica gel (50 g) eluted with CHCl3. The resulting oil (3.0 g, 79%) was homogeneous on tlc; Rf (CHCl3) 0.10; Rf (ether) 0.70; Rf (CHCl3 24, CH3OH 1) 0.55.

Workup

  1. filtrationthe solution was filtered through a column of neutral Al2O3 (100 g)
  2. washeluted with DMF
  3. customThe solvent was removed in vacuo
  4. filtrationthe residue filtered through a column of silica gel (50 g)
  5. washeluted with CHCl3

Sources & evidence

ORD record
ord-7fa926d4c6924511866ef7971fb1c9c6
Source dataset
uspto-grants-1980_12
Patent number
US04237046

Reaction notes

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