Triethylamine → HCID 131715439, compound

HRID 2414113Notes

Reaction equation

HRID 2414113 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13]([NH:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[O:14])([CH3:11])([CH3:10])[CH3:9].[C:21]([O:27][CH2:28]Cl)(=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23]>CN(C=O)C.C(OCC)(=O)C>[C:8]([O:12][C:13]([NH:15][CH2:16][CH2:17][C:18]([O:20][CH2:28][O:27][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[O:19])=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 87885Chloromethyl pivalate

Product 1

HCID 131715439HCID 131715439, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (32.4 ml) was added to N-tert.-butyloxycarbonyl β-alanine (40 g) in N,N'-dimethylformamide at room temperature under a nitrogen atmosphere in a 1 l round bottom flask. The solution was stirred 15 minutes and chloromethyl pivalate (36.6 g) [M. Rasmussen & N. J. Leonard, J. Amer. Chem. Soc., 89, 5439 (1967)] was added dropwise at 0° C. The solution was stirred at room temperature overnight. The mixture was then diluted with ethyl acetate, filtered, washed with water, then brine, and evaporated to give 70 g crude material which was chromatographed (silica gel) eluting with 15% ethyl acetate-hexane to give 62.5 g of product.

Workup

  1. stirringThe solution was stirred at room temperature overnight
  2. filtrationfiltered
  3. washwashed with water
  4. custombrine, and evaporated
  5. customto give 70 g crude material which
  6. customwas chromatographed (silica gel)
  7. washeluting with 15% ethyl acetate-hexane

Sources & evidence

ORD record
ord-9286872a65314f54990a2886194624d8
Source dataset
uspto-grants-1988_01
Patent number
US04721726

Reaction notes

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