Triethylamine → (R)-N5-(Cbz)-N2-(Diphenylacetyl)-(R)-N-[2-hydroxy-1-(4-methoxy-phenyl)ethyl]ornithine amide

HRID 366070Notes

Reaction equation

HRID 366070 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][C:27]([O:30][CH3:31])=[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([CH2:37][CH3:38])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][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1)[CH2:22][OH:23])=[O:19])[NH:17][C:22](=[O:23])[CH:21]([C:38]1[CH:37]=[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 131722076(R)-N5-(Cbz)-(R)-N-[2-hydroxy-1-(4-methoxyphenyl)ethyl]ornithine amide hydrochloride

Product 1

HCID 131722078(R)-N5-(Cbz)-N2-(Diphenylacetyl)-(R)-N-[2-hydroxy-1-(4-methoxy-phenyl)ethyl]ornithine amideYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared according to the method described in Example 1(d) above from (R)-N5 -(Cbz)-(R)-N-[2-hydroxy-1-(4-methoxyphenyl)ethyl]ornithine amide hydrochloride (3.33 g; 7.37 mmol; from step (b) above), 2-nitrophenyl diphenyl acetate (2.60 g; 8.10 mmol; see Example 1(c) above), triethylamine (2.23 g; 22.11 mmol) and CH2Cl2 (200 mL), reaction time 60 hours. The resulting yellow solution was submitted to aqueous work up, dried, filtered and concentrated to give the crude product as an off-white solid (4.76 g). The crude product was chromatographed twice on silica gel eluting with CH2Cl2 :MeOH (98:2). Concentration of the product containing fractions gave the sub-title compound as a white solid (0.63 g).

Workup

  1. customPrepared
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product as an off-white solid (4.76 g)
  6. customThe crude product was chromatographed twice on silica gel eluting with CH2Cl2 :MeOH (98:2)
  7. additionConcentration of the product containing fractions

Sources & evidence

ORD record
ord-8b8e9e8c545849e59cfdd28fc02361e6
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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