L-Alanine → HCID 131714115, compound

HRID 615692Notes

Reaction equation

HRID 615692 reaction equation
N(C(OC(C)(C)C)=O)[C@H](C(O)=[O:7])C(C)C.N[C@H](C(O)=O)C.[NH2:22][C@H:23]([C:27]([NH:29][CH2:30][C:31]([O:33]CC1C=CC=CC=1)=[O:32])=[O:28])[CH:24]([CH3:26])[CH3:25].CC1C=CC(S(O)(=O)=O)=CC=1.C1C=CC(COC(CN)=O)=CC=1.[OH:64][N:65]1[C:69]2[CH:70]=[CH:71][CH:72]=[CH:73][C:68]=2N=N1>O>[NH2:22][C@H:23]([C:27]([NH:29][CH2:30][C:31]([O:33][C:72]1[CH:73]=[CH:68][C:69]([N+:65]([O-:64])=[O:7])=[CH:70][CH:71]=1)=[O:32])=[O:28])[CH:24]([CH3:26])[CH3:25]

Participants

7

Reactant 5

HCID 5950L-AlanineHCID 757711-HydroxybenzotriazoleHCID 83693Boc-L-ValineHCID 6451311O-benzylglycine toluene-p-sulphonateHCID 14752533HCID 14752533, compound

Product 1

HCID 131714115HCID 131714115, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Synthesis: The synthesis of the peptide, Boc-Val-L. Pro-D. Ala-L. Val-Gly-OBzl (I), was carried out using classical solution methods starting from the C-terminal glycine benzyl ester p-tosylate. Each amino acid was coupled to the growing peptide chain by means of the water soluble carbodiimide 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) and 1-hydroxybenzotriazole. The tert-butyloxycarbonyl group was used for amino group protection, and its removal was achieved with trifluoroacetic acid. Peptide I was converted to the free acid by hydrogenolysis and then to the corresponding p-nitrophenyl ester using p-nitrophenyl trifluoroacetate. After deblocking the Nα -protecting group and neutralizing, H-L. Val-L. Pro-D. Ala-L. Val-Gly-ONp was polymerized in dimethyl sulfoxide for 14 days. The reaction mixture was diluted with water, dialyzed against water and lyophilized. Purity of all intermediate peptides was checked by thin layer chromatography and C-13 NMR spectra. The overall yields were 80-90% in the preparation of the intermediate products and 50% during the polymerization step.

Workup

  1. customSynthesis
  2. customThe tert-butyloxycarbonyl group was used for amino group protection, and its removal
  3. customdialyzed against water
  4. customThe overall yields
  5. customin the preparation of the intermediate products and 50%
  6. customduring the polymerization step

Sources & evidence

ORD record
ord-29f653acd49c4e30a59a432907488a01
Source dataset
uspto-grants-1985_02
Patent number
US04500700

Reaction notes

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