Triethylamine → (R)-N5-(Cbz)-N2-(Diphenylacetyl)-(S)-N-(2-hydroxy-1-phenylethyl)-ornithine amide

HRID 366054Notes

Reaction equation

HRID 366054 reaction equation
Cl.[C:2]([NH:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:18]([NH:20][C@H:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:22][OH:23])=[O:19])[NH2:17])([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].C(N([CH2:35][CH3:36])CC)C>C(Cl)Cl>[C:2]([NH:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:18]([NH:20][C@H:21]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:22][OH:23])=[O:19])[NH:17][C:22](=[O:23])[CH:21]([C:36]1[CH:35]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:3]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 131722057(R)-N5-(Cbz)-(S)-N-(2-hydroxy-1-phenylethyl)ornithine amide hydrochloride

Product 1

HCID 86755916(R)-N5-(Cbz)-N2-(Diphenylacetyl)-(S)-N-(2-hydroxy-1-phenylethyl)-ornithine amideYield 129.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared according to the method described in Example 1(d) above from (R)-N5 -(Cbz)-(S)-N-(2-hydroxy-1-phenylethyl)ornithine amide hydrochloride (2.0 g, 4.74 mmol; from step (b) above), 2-nitrophenyl diphenyl acetate (1.67 g; 5.21 mmol; see Example 1(c) above) and triethylamine (0.726 mL; 5.21 mmol) in 150 mL of CH2Cl2. The reaction mixture was heated to reflux for 1 hour, followed by standard aqueous work up, yielding 1.78 g of the sub-title compound as a white solid.

Workup

  1. customPrepared
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 1 hour

Sources & evidence

ORD record
ord-af2781fbe18643e18859699589a4afe9
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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