L-Tyrosine → HCID 178512890, compound

HRID 1164289Notes

Reaction equation

HRID 1164289 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:11]([NH:13][C@H:14]([C:36]([OH:38])=[O:37])[CH2:15][CH2:16][CH2:17][NH:18][C:19](=[NH:35])[NH:20]S(C1C(C)=C(C)C(OC)=CC=1C)(=O)=O)=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.N[C@H](C(O)=O)CCCNC(=N)N.N[C@H](C(O)=O)CC1C=CC(O)=CC=1>FC(F)(F)C(O)=O.C1(SC)C=CC=CC=1>[NH2:1][C@H:2]([C:11]([NH:13][C@H:14]([C:36]([OH:38])=[O:37])[CH2:15][CH2:16][CH2:17][NH:18][C:19](=[NH:20])[NH2:35])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6057L-TyrosineHCID 178418600HCID 178418600, compoundHCID 178491774HCID 178491774, compound

Product 1

HCID 178512890HCID 178512890, compound

Reagents, catalysts & solvents 1

HCID 67440411HCID 67440411, compoundSolvent

Procedure

In 5 ml of mixed solution of trifluoroacetic acid-thioanisole (9:1) was dissolved 400 mg of Boc-Tyr-Arg(Mtr)OH and the resulting mixture was allowed to stand at room temperature for 2 hours. The trifluoroacetic acid was distilled off under reduced pressure, ether was added to the residue and the resulting precipitate was collected by filtration. The precipitate was dissolved in a small amount of water, passed through a column (1×10 cm) of Amberlite IRA-410 (acetate-form) and lyophilized. The lyophilizate was dissolved in a small amount of water, chromatographed on a carboxymethyl-cellulose column (2.2×8 cm) and eluted by the linear gradient method using water (300 ml) and 0.1 M ammonium acetate (300 ml). The fractions from 100 to 150 ml were pooled and lyophilized. Yield 175 mg, [α]D21 -17.4° (c=0.5, H2O); amino acid analysis (acid hydrolysis): Arg 1.00(1), Tyr 0.94(1); average recovery 86.5%.

Workup

  1. distillationThe trifluoroacetic acid was distilled off under reduced pressure, ether
  2. additionwas added to the residue
  3. filtrationthe resulting precipitate was collected by filtration
  4. dissolutionThe precipitate was dissolved in a small amount of water
  5. dissolutionThe lyophilizate was dissolved in a small amount of water
  6. customchromatographed on a carboxymethyl-cellulose column (2.2×8 cm)
  7. washeluted by the linear gradient method
  8. customamino acid analysis (acid hydrolysis)

Sources & evidence

ORD record
ord-24b442b815774101a44308afbfcf6864
Source dataset
uspto-grants-1983_01
Patent number
US04368150

Reaction notes

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