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

HRID 366066Notes

Reaction equation

HRID 366066 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 131722070(R)-N5-(Cbz)-(S)-N-[2-hydroxy-1-(4-methoxyphenyl)ethyl]-ornithine amide hydrochloride

Product 1

HCID 131722072(R)-N5-(Cbz)-N2-(Diphenylacetyl)-(S)-N-[2-hydroxy-1-(4-methoxyphenyl)ethyl]ornithine amideYield 182.2%

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-(4-methoxyphenyl)ethyl]ornithine amide hydrochloride (2.32 g, 5.13 mmol; from step (b) above), 2-nitrophenyl diphenyl acetate (1.81 g; 5.65 mmol; see Example 1(c) above), triethylamine (0.78 g, 7.70 mmol) and CH2Cl2 (150 mL), 60 hours reaction time. The reaction mixture was submitted to aqueous work up, dried, filtered and concentrated to give the crude product as an off-white solid (3.39 g). The crude product was chromatographed on silica gel eluting with CH2C2 :MeOH (98:2). Concentration of the appropriate fractions gave pure sub-title compound as a white solid (2.85 g).

Workup

  1. customPrepared
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product as an off-white solid (3.39 g)
  6. customThe crude product was chromatographed on silica gel eluting with CH2C2

Sources & evidence

ORD record
ord-81670d6f724743409de27952eabdc4b0
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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