Di-tert-butyl dicarbonate → Ethyl acetate hexane

HRID 52200Notes

Reaction equation

HRID 52200 reaction equation
N([C:16]([O:18][C:19]([CH3:22])(C)C)=[O:17])[C@H:2]([CH2:14]O)[CH2:3][C:4]1C=C2C(C=CC=C2)=[CH:6][CH:5]=1.[C:23](OC(OC(C)(C)C)=O)(=O)OC(C)(C)C>C(O)(C)(C)C>[CH3:22][CH2:19][O:18][C:16]([CH3:23])=[O:17].[CH3:14][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 18660608Boc-Nal-CH2OH

Product 1

HCID 21226206Ethyl acetate hexaneYield 92%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Boc-Nal-CH2OH. L-naphthylalaninol (2.72 g; 13.5 mmol) was dissolved in tert-butanol (60 ml) and di-t-butyl pyrocarbonate (3.16 g; 14.5 mmol) was added. The reaction was stirred at room temperature for 3 h, then the solvent was removed in vacuo. A white solid was crystallized from AcOEt/hexane (3.47 g; 92% yield): mp 131°-132° C.

Workup

  1. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7beb0adae2e3484f87d1b90fabf90cc5
Source dataset
uspto-grants-1997_04
Patent number
US05616605

Reaction notes

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