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tert-Butyl acetate → N2-[(Phenylmethoxy)carbonyl]-L-lysine tert-Butyl Ester

HRID 1174
Notes
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Reaction equation

HRID 1174 reaction equation
[C:1]([NH:11][C@H:12]([C:18]([OH:20])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(O[C:25]([CH3:28])([CH3:27])[CH3:26])(=O)C.Cl(O)(=O)(=O)=O.[OH-].[Na+]>O.C(OCC)(=O)C>[C:1]([NH:11][C@H:12]([C:18]([O:20][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10908tert-Butyl acetateHCID 14798Sodium HydroxideHCID 24247Perchloric AcidHCID 75172N-alpha-Benzyloxycarbonyl-L-lysine

Product 1

HCID 11078219N2-[(Phenylmethoxy)carbonyl]-L-lysine tert-Butyl Ester

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 25 g of Nα-CBZ-L-lysine from Sigma, where CBZ is benzyloxycarbonyl, 250 mL of t-butyl acetate and 14 mL of 70% perchloric acid was vigorously mixed until all solids were dissolved. After stirring overnight, 375 mL of ethyl acetate was added followed by 250 mL of water. The pH of the aqueous layer was raised to 5.5 with 20% NaOH whereupon the organic phase was separated. The aqueous phase was extracted with the ethyl acetate solution and the pH again raised to 10.5 whereupon it was again extracted with 200 mL of fresh ethyl acetate. The organic extracts were combined, washed with saturated brine, dried over Na2SO4 and concentrated. The residue was dried overnight under high vacuum to yield 23.2 g of a colorless, viscous material.

Workup

  1. additionwas vigorously mixed until all solids
  2. dissolutionwere dissolved
  3. customwas separated
  4. extractionThe aqueous phase was extracted with the ethyl acetate solution
  5. temperaturethe pH again raised to 10.5 whereupon it
  6. extractionwas again extracted with 200 mL of fresh ethyl acetate
  7. washwashed with saturated brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe residue was dried overnight under high vacuum
  11. customto yield 23.2 g of a colorless, viscous material

Sources & evidence

ORD record
ord-138236e224a34c72b9402d81270c32cc
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723619

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes