Acetic Acid → HCID 131715814, compound

HRID 2291654

Reaction equation

HRID 2291654 reaction equation
[NH2:1][C@H:2]([C:14]([OH:16])=[O:15])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[C:17](O)(=[O:19])[CH3:18].O.CC(=O)OCC.C(OCC)C>CN(C=O)C>[NH:1]([C:17]([CH3:18])=[O:19])[C@H:2]([C:14]([OH:16])=[O:15])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 6993436(2S)-2-amino-5-(((tert-butoxy)carbonyl)amino)pentanoic acidHCID 21584169Diethylether ethylacetate

Product 1

HCID 131715814HCID 131715814, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.3 g of H-Orn(Boc)-OH, 5.0 g of the N-hydroxysuccinimide ester of acetic acid and 4.1 ml of NEM in 50 ml of DMF and 10 ml of H2O are allowed to react at room temperature for 3 days. The solvent is evaporated off in vacuo, and the residue is chromatographed on silica gel (system 4). 9.6 g of Ac-Orn(Boc)-OH (yield: 88%) readily crystallize from EA/diethyl ether. MS (FAB): 275 (M+1).

Workup

  1. customto react at room temperature for 3 days
  2. customThe solvent is evaporated off in vacuo
  3. customthe residue is chromatographed on silica gel (system 4)

Sources & evidence

ORD record
ord-cc0225c8c0df4c3c8555c5cce744e32b
Source dataset
uspto-grants-1989_01
Patent number
US04797471

Linked notes

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