Pyridine → Benzyloxycarbonyl-L-asparaginyl-Nepsilon-tert.butyloxycarbonyl-L-lysine

HRID 1284042Notes

Reaction equation

HRID 1284042 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C@@H:13]([C:15]([OH:17])=[O:16])[NH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N+](CC)(CC)CC)C1C=CC=CC=1.[N+](C1C=CC([O:41][C:42](=O)[C@H:43]([CH2:55][C:56](=[O:58])[NH2:57])[NH:44][C:45]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[O:46])=CC=1)([O-])=O.N1C=CC=CC=1>CN(C)C=O>[CH2:48]([O:47][C:45]([NH:44][C@H:43]([C:42]([NH:14][C@H:13]([C:15]([OH:17])=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:41])[CH2:55][C:56](=[O:58])[NH2:57])=[O:46])[C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 17208BenzyltriethylammoniumHCID 2733283(2S)-2-amino-6-(((tert-butoxy)carbonyl)amino)hexanoic acidHCID 7021351Z-Asn-onp

Product 1

HCID 22792312Benzyloxycarbonyl-L-asparaginyl-Nepsilon-tert.butyloxycarbonyl-L-lysine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

51 g Nε-tert.butyloxycarbonyl-L-lysine were converted in a conventional manner into the benzyltriethylammonium salt and then stirred in 700 ml dimethylformamide with 81 g benzyloxycarbonyl-L-asparagine-4-nitrophenyl ester with the addition of 1 equivalent of pyridine for 48 hours at 20°. The residue left after vacuum evaporation was treated with ethyl acetate and potassium hydrogen sulfate solutions simultaneously; the thick precipitate formed was filtered off and then recrystallised from ethanol/petroleum ether. F = 174° - 175° (Z);[α]D20 = + 13.8° (c = 1.0; in pyridine). Yield = 70 g (71 % of the theoretical amount).

Workup

  1. waitThe residue left
  2. customafter vacuum evaporation
  3. additionwas treated with ethyl acetate and potassium hydrogen sulfate solutions simultaneously
  4. customthe thick precipitate formed
  5. filtrationwas filtered off
  6. customrecrystallised from ethanol/petroleum ether
  7. customF = 174° - 175° (Z)
  8. custom[α]D20 = + 13.8° (c = 1.0; in pyridine)

Sources & evidence

ORD record
ord-0a20e8faeede409f8ccf6455d7ba22bc
Source dataset
uspto-grants-1976_08
Patent number
US03978035

Reaction notes

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