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

HRID 366064Notes

Reaction equation

HRID 366064 reaction equation
[N+](C1C=CC=CC=1O[C:11](=[O:35])[C@@H:12]([CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([O-])=O.Cl.[CH3:37][O:38][C:39]1[CH:48]=[CH:47][C:42]([C@H:43]([NH2:46])[CH2:44][OH:45])=[CH:41][CH:40]=1.CCN(C(C)C)C(C)C.Cl>C(Cl)Cl.[Cl-].[Na+].O.O.C(N(CC)CC)C>[C:14]([NH:13][C@H:12]([C:11]([NH:46][C@H:43]([C:42]1[CH:47]=[CH:48][C:39]([O:38][CH3:37])=[CH:40][CH:41]=1)[CH2:44][OH:45])=[O:35])[CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 54461433Nalpha-Boc-Ndelta-Cbz-(R)-ornithine o-nitrophenyl esterHCID 70141372(S)-2-Amino-2-(4-methoxyphenyl)ethanol hydrochloride

Product 1

HCID 131722069(R)-N2-(Boc)-N5-(Cbz)-(S)-N-[2-hydroxy-1-(4-methoxyphenyl)ethyl]ornithine amideYield 78.3%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Prepared according to the method described in Example 11(a) above from Nα -Boc-Nδ -Cbz-(R)-ornithine o-nitrophenyl ester (4.83 g; 9.91 mmol; see Example 4(a) above) with (S)-4-methoxy-α-hydroxymethylbenzylamine hydrochloride (2.22 g; 10.90 mmol) and triethylamine (1.50 g; 14.87 mmol; instead of DiPEA) in CH2Cl2 (150 mL), 18 hours reaction time. The reaction mixture was submitted to aqueous work up using water, 1N HCl and brine. The organic solution was dried, filtered and concentrated to give the sub-title compound as a yellow solid (4.0 g) which was used without purification.

Workup

  1. customPrepared
  2. customThe organic solution was dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b28ed462667a447da2d49c4348357e3d
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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