4-Methylmorpholine → N-Benzyloxy-alpha-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetamide

HRID 727531Notes

Reaction equation

HRID 727531 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[O:13]=[C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](=[O:23])[N:15]1[CH2:24][CH2:25][CH:26]([C:30]1([CH2:44][CH:45]([CH3:47])[CH3:46])[CH2:34][CH2:33][N:32]([CH2:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]1=[O:43])[C:27](O)=[O:28].Cl.[CH2:49]([O:56][NH2:57])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.CN1CCOCC1>C(Cl)Cl>[CH2:49]([O:56][NH:57][C:27](=[O:28])[CH:26]([CH2:25][CH2:24][N:15]1[C:14](=[O:13])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:23])[C:30]1([CH2:44][CH:45]([CH3:46])[CH3:47])[CH2:34][CH2:33][N:32]([CH2:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:31]1=[O:43])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 102312Benzyloxyamine hydrochlorideHCID 19705466alpha-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetic Acid

Product 1

HCID 19705472N-Benzyloxy-alpha-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetamideYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

CDI (82 mg, 0.51 mmol) is added to a solution of α-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetic acid (202 mg, 0.424 mmol) and CH2Cl2 (3.2 mL) at room temperature, and the solution is stirred for 1 hour at room temperature. O-Benzylhydroxylamine hydrochloride (98 mg, 0.614 mmol) and 4-methylmorpholine (84 uL, 0.76 mmol) are added in succession, and the solution is allowed to stir overnight at room temperature. Aqueous workup (CH2Cl2, MgSO4) and purification by column chromatography (2% acetene/CH2Cl2) gives 120 mg (49%) of the title compound as a colorless oil.

Workup

  1. stirringto stir overnight at room temperature
  2. customAqueous workup (CH2Cl2, MgSO4) and purification by column chromatography (2% acetene/CH2Cl2)

Sources & evidence

ORD record
ord-37b3c58edb8f4f1584a4cab4acec1a1b
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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