2,2-Diphenylacetyl chloride → HCID 131722041, compound

HRID 366042Notes

Reaction equation

HRID 366042 reaction equation
Cl.C([NH:9][C@@H:10]([C:25]([NH:27][C@@H:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH3:29])=[O:26])[CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])(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:15]([NH:14][CH2:13][CH2:12][CH2:11][C@H:10]([C:25]([NH:27][C@@H:28]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH3:29])=[O:26])[NH:9][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:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16]

Participants

8

Reactant 4

HCID 746372,2-Diphenylacetyl chlorideHCID 81531DiisopropylethylamineHCID 21866389Hydrogen chloride-ethyl acetateHCID 131722042HCID 131722042, compound

Product 1

HCID 131722041HCID 131722041, compoundYield 24%

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)-(R)-N-(1-phenylethyl)ornithine amide hydrochloride (5.9 g; 13 mmol; from step (a) above) EtOAc (30 mL) then HCl/EtOAc (100 mL), 3.5 hours reaction time for the deprotection, then CH2Cl2 (100 mL), diphenylacetyl chloride (2.9 g; 13 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 organic layer was partially concentrated at reduced pressure, upon which a precipitate formed, which was filtered to give 1.7 g (24%) of the sub-title compound as a solid.

Workup

  1. customPrepared
  2. customovernight reaction time
  3. concentrationThe organic layer was partially concentrated at reduced pressure, upon which a precipitate
  4. customformed
  5. filtrationwhich was filtered

Sources & evidence

ORD record
ord-4caba199885240cb95f72bf6d214bbcf
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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