Ethanol → N-(tert-Butoxycarbonyl)-D-alanyl-N-methyl-L-leucine

HRID 1583845Notes

Reaction equation

HRID 1583845 reaction equation
[NH:1]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@@H:2]([C:4]([N:6]([CH3:21])[C@H:7]([C:12](CC1C=CC=CC=1)=[O:13])[CH2:8][CH:9]([CH3:11])[CH3:10])=[O:5])[CH3:3].C([OH:31])C>>[NH:1]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@@H:2]([C:4]([N:6]([CH3:21])[C@H:7]([C:12]([OH:13])=[O:31])[CH2:8][CH:9]([CH3:10])[CH3:11])=[O:5])[CH3:3]

Participants

3

Reactant 2

HCID 702EthanolHCID 131714440HCID 131714440, compound

Product 1

HCID 13254981N-(tert-Butoxycarbonyl)-D-alanyl-N-methyl-L-leucine

Procedure

32.45 g (79.92 m mol) BOC-(D)-Ala-MeLeu-Bzl in 800 ml ethanol containing 1.6 g 10% palladium/charcoal are debenzylated by hydrogenation for 2 hours at room temperature. After uptake of the calculated quantity of hydrogen the suspension is filtered through talc, the solvent evaporated off and the residue crystallised from hexane to yield the title compound with a rotation of [α]D25 =-36.7° (c=0.8 in chloroform).

Workup

  1. filtrationAfter uptake of the calculated quantity of hydrogen the suspension is filtered through talc
  2. customthe solvent evaporated off
  3. customthe residue crystallised from hexane

Sources & evidence

ORD record
ord-936883caa7ec41099acb2254700dafdd
Source dataset
uspto-grants-1985_11
Patent number
US04554351

Reaction notes

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