1-Hydroxybenzotriazole → (R)-N2-(Boc)-N5-(Cbz)-N-methyl-(R)-N-(1-phenylethyl)ornithine amide

HRID 366076Notes

Reaction equation

HRID 366076 reaction equation
[C:1]([NH:8][C@@H:9]([C:24]([OH:26])=O)[CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:73][NH:74][C@H:75]([CH3:82])[C:76]1[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1>C(#N)C.C(Cl)Cl>[C:1]([NH:8][C@@H:9]([C:24]([N:74]([CH3:73])[C@@H:75]([C:76]1[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1)[CH3:82])=[O:26])[CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2060888(R)-(+)-N-Methyl-1-phenylethylamineHCID 7272030N2-((1,1-Dimethylethoxy)carbonyl)-N5-((phenylmethoxy)carbonyl)-D-ornithine

Product 1

HCID 131722083(R)-N2-(Boc)-N5-(Cbz)-N-methyl-(R)-N-(1-phenylethyl)ornithine amideYield 95.4%

Reagents, catalysts & solvents 1

HCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

Prepared according to the method described in Example 1(a) above from Nα -Boc-Nδ -Cbz-(R)-ornithine (5.0 g; 13 mmol), BOP reagent (6.0 g; 13 mmol), HOBT (1.8 g; 13 mmol), DiPEA (7.1 mL; 40 mmol) and acetonitrile:CH2Cl2 (1:1; 100 mL) followed by (R)-(+)-N,α-dimethylbenzylamine (2.0 mL; 13 mmol), then stirred overnight. After work up the crude product was purified by chromatography on silica gel with EtOAc to provide 6.0 g (91%) of the sub-title compound.

Workup

  1. customPrepared
  2. customAfter work up the crude product was purified by chromatography on silica gel with EtOAc

Sources & evidence

ORD record
ord-afac093e37bc456fb9ac57210798b7e9
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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