Acetic Acid → N2 [(1,1-Dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysine, ethyl ester

HRID 231946

Reaction equation

HRID 231946 reaction equation
N#N.[CH3:3][C:4]([CH3:29])([O:6][C:7]([NH:9][C@H:10]([C:26]([OH:28])=[O:27])[CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=[O:8])[CH3:5].[N+:30](=C)=[N-:31].[C:33](O)(=O)[CH3:34].N#N.CC(C)(OC(N[C@H](C(OC)=O)CCCCNC(OCC1C=CC=CC=1)=O)=O)C>C(OCC)(=O)C.CC(C)=O.CCCCCC>[N:30]#[N:31].[CH3:5][C:4]([CH3:29])([O:6][C:7]([NH:9][C@H:10]([C:26]([O:28][CH2:33][CH3:34])=[O:27])[CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])=[O:8])[CH3:3]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 86742311N2 [(1,1-dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysineHCID 131714291N2 [(1,1-Dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysine, methyl ester

Product 1

HCID 131716012N2 [(1,1-Dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysine, ethyl ester

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N2 -[(1,1-Dimethylethoxy)carbonyl]-N6 -[(phenylmethoxy)carbonyl]-L-lysine (5.48 g., 14.4 mmole) is dissolved in ethyl acetate (130 ml.). Diazomethane is added until a yellow color persists. Acetic acid is added to quench the excess diazomethane, and the volatiles are evaporated. The residue is partitioned between ethyl acetate and saturated sodium bicarbonate, the organic layer is dried over sodium sulfate, filtered, and then the volatiles are evaporated. Purification of the residue by column chromatography on LPS-1 silica eluting with 30% ethyl acetate/hexane yields 4.0 g. of N2 -[(1,1-dimethylethoxy)carbonyl]-N6 -[(phenylmethoxy)carbonyl]-L-lysine, methyl ester. TLC (silica gel; hexane:acetone, 1:1) Rf =0.69.

Workup

  1. customto quench the excess diazomethane
  2. customthe volatiles are evaporated
  3. customThe residue is partitioned between ethyl acetate and saturated sodium bicarbonate
  4. dry with materialthe organic layer is dried over sodium sulfate
  5. filtrationfiltered
  6. customthe volatiles are evaporated
  7. customPurification of the residue by column chromatography on LPS-1 silica eluting with 30% ethyl acetate/hexane
  8. customyields 4.0 g

Sources & evidence

ORD record
ord-21245ab6dfb242aea21b6a51d4edb4cb
Source dataset
uspto-grants-1989_07
Patent number
US04849414

Linked notes

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