Trifluoroacetic acid → Nalpha,Ndelta-Bis-Boc-D-ornithyl-N-(phenethyl)glycine 2-Naphthylamide

HRID 1067079Notes

Reaction equation

HRID 1067079 reaction equation
[C:1]([NH:8][C@@H:9]([C:21]([OH:23])=O)[CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(C(C)C)CC)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH:57]1[C:66]2[C:61](=[CH:62][CH:63]=[CH:64][CH:65]=2)[CH:60]=[CH:59][C:58]=1[NH:67][C:68](=[O:86])[CH2:69][N:70](C(OC(C)(C)C)=O)[CH2:71][CH2:72][C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:57]1[C:66]2[C:61](=[CH:62][CH:63]=[CH:64][CH:65]=2)[CH:60]=[CH:59][C:58]=1[NH:67][C:68](=[O:86])[CH2:69][N:70]([C:21](=[O:23])[C@@H:9]([CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:71][CH2:72][C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 81531Diisopropylethylamine2×HCID 2733179PyBroPHCID 7015801HCID 7015801, compoundHCID 21195850Boc-N-(phenethyl)glycine 2-naphthylamide

Product 1

HCID 20662194Nalpha,Ndelta-Bis-Boc-D-ornithyl-N-(phenethyl)glycine 2-Naphthylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution (0° C.) of Nα,Nδ-bis-Boc-D-ornithine (130 mg, 0.39 mmol), diisopropylethylamine (1.6 mmol) and methylene chloride (10 mL) was treated with PyBroP (275 mg, 0.59 mmol) and kept at 0° C. for 30 min. In another reaction, a solution of Boc-N-(phenethyl)glycine 2-naphthylamide (240 mg, 0.59 mmol) (made by coupling of N-Boc-N-(phenethyl)glycine and 2-naphthylamine) and trifluoroacetic acid (3 mL) was stored at 24° C. for 1 hr and then concentrated in vacuo. The residue was coevaporated twice with methylene chloride and the resultant solid resuspended in methylene chloride (10 mL) and treated with diisopropylethylamine (1.2 mmol). The two solutions were mixed and stirred at 25° C. for 1 hr at which time the mixture was washed with 1M hydrochloric acid (2×25 mL), sat. sodium bicarbonate (25 mL), and brine (25 mL). The organic layer was dried over anhydrous sodium sulfate and adsorbed onto silica gel (500 mg) and applied to a column prepacked with silica gel. The column was eluted with ethyl acetate:hexane (50:50, v:v) to afford the titled compound.

Workup

  1. customIn another reaction
  2. concentrationconcentrated in vacuo
  3. additionThe two solutions were mixed
  4. washwas washed with 1M hydrochloric acid (2×25 mL), sat. sodium bicarbonate (25 mL), and brine (25 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. washThe column was eluted with ethyl acetate:hexane (50:50, v:v)

Sources & evidence

ORD record
ord-20d1efb98bf347588c2e1eab785817b9
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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