Hydrochloric Acid → N-Benzyloxy-alpha-methyl-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetamide

HRID 727525Notes

Reaction equation

HRID 727525 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:13][CH:14]([C:18]1([CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]1=[O:31])[C:15]([OH:17])=O.[CH2:36]([O:43][NH2:44])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.Cl.CN1CCOCC1>C(Cl)Cl>[CH2:36]([O:43][NH:44][C:15](=[O:17])[CH:14]([CH3:13])[C:18]1([CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]1=[O:31])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 102313O-BenzylhydroxylamineHCID 19705475alpha-Methyl-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetic Acid

Product 1

HCID 19705438N-Benzyloxy-alpha-methyl-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetamideYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

CDI (39.7 mg, 0.245 mmol) is added to a solution of α-methyl-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetic acid (74.0 mg, 0.233 mmol) and CH2Cl2 (2.0 mL). The solution is stirred for 1 hour at room temperature. To this is added O-benzylhydroxylamine.HCl (63.2 mg, 0.396 mmol) and N-methylmorpholine (44 μL, 0.40 mmol). The resultant solution is stirred for 16 hours at room temperature. Aqueous workup (CH2Cl2, MgSO4) and purification by flash chromatography (2:1 EtOAc:hexane) gives 88.1 mg (89%) of the title compound as an oil.

Workup

  1. customAqueous workup (CH2Cl2, MgSO4) and purification by flash chromatography (2:1 EtOAc:hexane)

Sources & evidence

ORD record
ord-709eb8b675e248fd94c2a6af79eac1f4
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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