Diisopropylethylamine → (R)-N2-(Boc)-N5-(Cbz)-(S)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amide

HRID 366073Notes

Reaction equation

HRID 366073 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].[OH:27][C:28]1[CH:36]=[CH:35][C:31]([C@@H:32]([NH2:34])[CH3:33])=[CH:30][CH:29]=1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(#N)C.C(#N)C.C(Cl)Cl.C(N(CC)CC)C>[C:1]([NH:8][C@H:9]([C:24]([NH:34][C@@H:32]([C:31]1[CH:35]=[CH:36][C:28]([OH:27])=[CH:29][CH:30]=1)[CH3:33])=[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

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 7272030N2-((1,1-Dimethylethoxy)carbonyl)-N5-((phenylmethoxy)carbonyl)-D-ornithineHCID 41097924(S)-4-(1-Aminoethyl)phenol

Product 1

HCID 86755920(R)-N2-(Boc)-N5-(Cbz)-(S)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amideYield 94.8%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolventHCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

Prepared according to the method described in Example 1(a) above from Nα -Boc-Nδ -Cbz-(R)-ornithine (5.34 g; 14.56 mmol), (S)-4-hydroxy-α-methylbenzylamine (2.0 g; 14.56 mmol), BOP reagent (9.67 g; 21.9 mmol), triethylamine (2.5 mL; instead of DiPEA) in acetonitrile (100 mL; instead of acetonitrile:CH2Cl2 (1:1)) to yield the sub-title compound (6.7g) as a white foam. The crude 1H NMR was consistent with the structure.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-054021804d634baeba687d8fb2c87f5b
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

Loading…