Diethylamine → methyl(2S)-3,3-dimethyl-2-{3-[(1-methyl-1H-benzimidazol-2-yl)methyl]-2-oxoimidazolidin-1-yl}butanoate

HRID 216287

Reaction equation

C1C2C(C[O:15][C:16]([N:18]([CH2:31][C:32]3[N:36]([CH3:37])[C:35]4[CH:38]=[CH:39][CH:40]=[CH:41][C:34]=4[N:33]=3)[CH2:19][CH2:20][NH:21][C@@H:22]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:23]([O:25][CH3:26])=[O:24])=O)C3C(=CC=CC=3)C=2C=CC=1.C(NCC)C.C(=O)(OC1C=CC([N+]([O-])=O)=CC=1)OC1C=CC([N+]([O-])=O)=CC=1>CN(C)C=O.ClC(Cl)C>[CH3:30][C:27]([CH3:29])([CH3:28])[C@H:22]([N:21]1[CH2:20][CH2:19][N:18]([CH2:31][C:32]2[N:36]([CH3:37])[C:35]3[CH:38]=[CH:39][CH:40]=[CH:41][C:34]=3[N:33]=2)[C:16]1=[O:15])[C:23]([O:25][CH3:26])=[O:24]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of the product of Example 148D (0.19 g) in N,N-dimethylformamide (3.5 mL) was treated with diethylamine (0.35 mL), stirred at 25° C. for 1.5 hours and concentrated. A solution of the residue in dichloroethane (7 mL) was treated with bis-(p-nitrophenyl) carbonate (0.128 g, 1.2 equivalents), stirred at 60° C. for 16 hours and concentrated. The residue was chromatographed on silica gel, eluting with ethyl acetate:dichloromethane (3:2) to give 80 mg (64%) of the title compound.

Workup

concentrationconcentrated
stirringstirred at 60° C. for 16 hours
concentrationconcentrated
customThe residue was chromatographed on silica gel
washeluting with ethyl acetate:dichloromethane (3:2)

Sources & evidence

ORD record: ord-b55997fdd53846e78ed6c4674a48a0e7
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193227B2

Linked notes

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