Triethylamine → 2-(N-(tert.-Butoxycarbonyl)-L-phenylalanyl-aminooxy)-acetic acid

HRID 426962Notes

Reaction equation

HRID 426962 reaction equation
Br.[NH2:2][O:3][CH2:4][C:5]([OH:7])=[O:6].[CH3:8][C:9]([O:12][C:13]([NH:15][C@H:16]([C:24](ON1C(=O)CCC1=O)=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])([CH3:11])[CH3:10].C(N(CC)CC)C>CN(C=O)C.C(O)C>[C:9]([O:12][C:13]([NH:15][C@H:16]([C:24]([NH:2][O:3][CH2:4][C:5]([OH:7])=[O:6])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])([CH3:10])([CH3:11])[CH3:8]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 107447tert-Butyl (S)-(1-benzyl-2-((2,5-dioxo-1-pyrrolidinyl)oxy)-2-oxoethyl)carbamateHCID 85822048Aminooxy-acetic acid hydrobromide

Product 1

HCID 228088902-(N-(tert.-Butoxycarbonyl)-L-phenylalanyl-aminooxy)-acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

6.97 g (40.5 mmoles) of aminooxy-acetic acid hydrobromide are reacted with 14.68 g (40.5 mmoles) of BOC--Phe--OSu in 100 ml of DMF in the presence of 6.3 ml (45 mmoles) of triethylamine. Next day the reaction mixture is evaporated in vacuo, the oily residue is dissolved in 100 ml of chloroform, and the chloroform solution is washed thrice with 1 n hydrochloric acid. The organic solution is dried, evaporated in vacuo, and the oily residue is solidified with diisopropyl ether. The crude product is purified by precipitation from an ethyl acetate-diisopropyl ether solvent system. 9.70 g (74%) of BOC--Phe--OGly--OH are obtained; m.p.: 136°-137° C., Rf5 : 0.4, [α]D : -17.8° (c: 1.0, in ethanol).

Workup

  1. customNext day the reaction mixture is evaporated in vacuo
  2. dissolutionthe oily residue is dissolved in 100 ml of chloroform
  3. washthe chloroform solution is washed thrice with 1 n hydrochloric acid
  4. customThe organic solution is dried
  5. customevaporated in vacuo
  6. customThe crude product is purified by precipitation from an ethyl acetate-diisopropyl ether solvent system
  7. custom9.70 g (74%) of BOC--Phe--OGly--OH are obtained

Sources & evidence

ORD record
ord-93db830dfaa0488fae758e9a32a52970
Source dataset
uspto-grants-1979_10
Patent number
US04172130

Reaction notes

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