Acetate → HCID 86757009, compound

HRID 1067086Notes

Reaction equation

HRID 1067086 reaction equation
[C:1]([NH:8][CH2:9][C:10]([OH:12])=O)([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:46]1([CH2:52][CH2:53][CH2:54][NH:55][C:56](=[O:78])[C@H:57]([CH2:67][CH2:68][CH2:69][NH:70][C:71]([O:73][C:74]([CH3:77])([CH3:76])[CH3:75])=[O:72])[NH:58][CH2:59][CH2:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.C([O-])(=O)C>O1CCCC1>[C:46]1([CH2:52][CH2:53][CH2:54][NH:55][C:56](=[O:78])[C@H:57]([CH2:67][CH2:68][CH2:69][NH:70][C:71]([O:73][C:74]([CH3:76])([CH3:75])[CH3:77])=[O:72])[N:58]([C:10](=[O:12])[CH2:9][NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:59][CH2:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1

Participants

7

Reactant 5

HCID 175AcetateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 86757010HCID 86757010, compound

Product 1

HCID 86757009HCID 86757009, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

cold solution (0° C.) of Boc-glycine (543 mg, 3.1 mmol), diisopropylethylamine (1 ml, 6.2 mmol), and tetrahydrofuran (10 ml) was treated with PyBrop (1.45 g, 3.1 mmol), followed by the addition of Nα-phenethyl-Nδ-Boc-ornithine 3-phenylpropylamide (1.28 g, 2.8 mmol) in tetrahydrofuran (5 ml). The resulting solution was acetate. The filtrate was concentrated in vacuo and the product purified by chromatography (silica gel—hexane/ethyl acetate) to give N-Boc-glycyl-Nα-phenethyl-Nδ-Boc-ornithine 3-phenylpropylamide (1.2 g).

Workup

  1. concentrationThe filtrate was concentrated in vacuo
  2. customthe product purified by chromatography (silica gel—hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cc92c5c6e0314d6eb2a910918d9d4c8c
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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