Diisopropylethylamine → HCID 86757004, compound

HRID 1067082Notes

Reaction equation

HRID 1067082 reaction equation
[C:1]([NH:8][C@H:9]([C:18]([OH:20])=O)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([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.[C:54]1([CH2:60][CH2:61][CH2:62][NH:63][C:64](=[O:79])[C@H:65]([CH2:68][CH2:69][CH2:70][NH:71][C:72]([O:74][C:75]([CH3:78])([CH3:77])[CH3:76])=[O:73])[NH:66][CH3:67])[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>O1CCCC1>[C:54]1([CH2:60][CH2:61][CH2:62][NH:63][C:64](=[O:79])[C@H:65]([CH2:68][CH2:69][CH2:70][NH:71][C:72]([O:74][C:75]([CH3:77])([CH3:76])[CH3:78])=[O:73])[N:66]([C:18](=[O:20])[C@H:9]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH3:67])[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 7018726(2S)-2-(((tert-butoxy)carbonyl)amino)-4-phenylbutanoic acidHCID 86757005HCID 86757005, compound

Product 1

HCID 86757004HCID 86757004, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A cold solution (0° C.) of N-Boc-homophenylalanine (221 mg), diisopropylethylamine (228 μl), and anhydrous tetrahydrofuran (4 ml) was treated with PyBrop (398 mg), followed by the addition of a solution of Nδ-Boc-Nα-methylornithine 3-phenylpropylamide (228 mg) in tetrahydrofuran (3 ml). The resulting solution was stirred for overnight. The precipitate was filtered and the solid was washed with ethyl acetate. The filtrate was concentrated in vacuo and the product purified by silica gel chromatography (hexane/ethyl acetate) to give N-Boc-homophenylalanyl-Nδ-Boc-Nα-methylornithine 3-phenylpropylamide (260 mg): 1H NMR (400 MHz, CDCl3) δ1.43 (s, 18H), 1.7-2.0 (m, 8H), 2.58 (t, J=6.4 Hz, 2H), 2.6-2.85 (m, 5H), 3.0-3.4 (m, 4H), 4.4-4.5 (m, 1H), 4.9-5.0 (m, 1H), and 7.1-7.3 (m, 10H).

Workup

  1. filtrationThe precipitate was filtered
  2. washthe solid was washed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe product purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-320162e98ceb42aea53a31ef7f127745
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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