2,2-Diphenylacetyl chloride → (R)-N5-(Cbz)-N2-(Diphenylacetyl)-N-methyl-(S)-N-(1-phenylethyl)-ornithine amide

HRID 366079Notes

Reaction equation

HRID 366079 reaction equation
C([NH:8][C@H:9]([C:24]([N:26]([CH3:35])[C@@H:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH3:28])=[O:25])[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])(OC(C)(C)C)=O.Cl.CCOC(C)=O.[C:43]1([CH:49]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C:50](Cl)=[O:51])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.N1C=CC=CC=1.CCOC(C)=O>[C:14]([NH:13][CH2:12][CH2:11][CH2:10][C@@H:9]([C:24]([N:26]([CH3:35])[C@@H:27]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH3:28])=[O:25])[NH:8][C:50](=[O:51])[CH:49]([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15]

Participants

8

Reactant 4

HCID 746372,2-Diphenylacetyl chlorideHCID 81531DiisopropylethylamineHCID 21866389Hydrogen chloride-ethyl acetateHCID 131722087HCID 131722087, compound

Product 1

HCID 131722086(R)-N5-(Cbz)-N2-(Diphenylacetyl)-N-methyl-(S)-N-(1-phenylethyl)-ornithine amideYield 30%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Prepared according to the method described in Examples 2(b) and 2(c) above from (R)-N2 -(Boc)-N5 -(Cbz)-N-methyl-(S)-N-(1-phenylethyl)-ornithine amide (5.3 g; 11 mmol; from step (a) above), EtOAc (75 mL), then HCl/EtOAc (75 mL), 2.5 hours reaction time for the deprotection, then CH2Cl2 (50 mL), diphenylacetyl chloride (2.6 g; 11 mmol) followed by pyridine (3.0 mL; 37 mmol; instead of DiPEA) over 1 min, overnight reaction time, diluted with CH2Cl2 (100 mL) for the work-up procedure. The crude material was purified by chromatography on silica gel with EtOAc:hexane (1:1) to provide 1.9 g (30%) of the sub-title compound.

Workup

  1. customPrepared
  2. customovernight reaction time
  3. customThe crude material was purified by chromatography on silica gel with EtOAc:hexane (1:1)

Sources & evidence

ORD record
ord-1b7ada4827c94454b0609963f2fca093
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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