Gamma-Aminobutyric Acid → 4-(((Benzyloxy)carbonyl)amino)butanoic acid

HRID 1632539Notes

Reaction equation

HRID 1632539 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH2:8]([O:15][C:16](ON1C(=O)CCC1=O)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C=O)C>[CH2:8]([O:15][C:16]([NH:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 119Gamma-Aminobutyric AcidHCID 83172Benzyl succinimido carbonate

Product 1

HCID 211844-(((Benzyloxy)carbonyl)amino)butanoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Gamma-aminobutyric acid (1.03 g:0.010 mol) and N-benzyloxycarbonyloxysuccinimide (2.49 g:0.01 mol) in N,N'-dimethylformamide (10 ml) was stirred for 18 hours at 22° C. The resulting clear solution was concentrated and the residue was treated with water. The resulting oil yielded white crystals which were then dried to yield a residue which was purified on a silica gel column employing dichloromethane:methanol mixture (95:5) as an eluent to yield gamma-(benzyloxycarbonylamino)butyric acid.

Workup

  1. concentrationThe resulting clear solution was concentrated
  2. additionthe residue was treated with water
  3. customThe resulting oil yielded white crystals which
  4. customwere then dried
  5. customto yield a residue which
  6. customwas purified on a silica gel column

Sources & evidence

ORD record
ord-18df410d6a30489d9a284e4ca3b2f297
Source dataset
uspto-grants-1984_10
Patent number
US04476229

Reaction notes

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