Hydrochloric Acid → HCID 178454154, compound

HRID 1906133Notes

Reaction equation

HRID 1906133 reaction equation
[NH2:1][C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:12])[NH:8][N+:9]([O-:11])=[O:10].Cl.[NH:17]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@H:18]([C:26](O)=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CS(C1N=CC=CN=1)C>CN(C=O)C.CCOC(C)=O>[NH:17]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@H:18]([C:26]([NH:1][C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:12])[NH:8][N+:9]([O-:11])=[O:10])=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 178504131HCID 178504131, compoundHCID 178512188HCID 178512188, compound

Product 1

HCID 178454154HCID 178454154, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Next, 31.3 g (0.08 mole) of H-Arg(NO2)-CHA.HCl was dissolved in 160 ml of 1.5N-NEM/DMF, to this solution was added 31.0 g (0.08 mole) of BOC-Phe-SDP (dimethylmercaptopyrimidine) at 0° to 5° C. and reacted for 18 hours. After the reaction was completed, the reaction mixture was diluted with 1600 ml of AcOEt, and washed twice with 400 ml of cold 5% hydrochloric acid, and washed twice with 400 ml of an aqueous solution saturated with sodium chloride, then there was precipitated crystals. The crystals thus precipitated were collected by filtration and dried to obtain crude BOC-Phe-Arg(NO2)-CHA, then recrystallized from AcOEt/n-hexane to obtain 35.1 g (72.9%) of BOC-Phe-Arg(NO2)-CHA.

Workup

  1. customreacted for 18 hours
  2. washwashed twice with 400 ml of cold 5% hydrochloric acid
  3. washwashed twice with 400 ml of an aqueous solution saturated with sodium chloride
  4. customthere was precipitated crystals
  5. customThe crystals thus precipitated
  6. filtrationwere collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-bdd12e21646c4611b0cf672e6f77f8bd
Source dataset
uspto-grants-1987_03
Patent number
US04650753

Reaction notes

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