Triethylamine → tert-butyl(2S)-3,3-dimethyl-2-{3-[(6-methyl-2-pyridinyl)methyl]-2-oxo-1-imidazolidinyl}butanoate

HRID 1174141Notes

Reaction equation

[CH3:1][C:2]([CH3:24])([CH3:23])[C@H:3]([NH:11][CH2:12][CH2:13][NH:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=1)[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)[C:27](=[O:28])C1.C(N(CC)CC)C>ClCCCl>[CH3:1][C:2]([CH3:24])([CH3:23])[C@H:3]([N:11]1[CH2:12][CH2:13][N:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=2)[C:27]1=[O:28])[C:4]([O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:5]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution containing the product from Example 10A (1.76 g, 5.25 mmol) in 1,2-dichloroethane (210 mL) was treated with N,N-disuccinimidyl carbonate (1.61 g, 6.28 mmol) and triethylamine (0.75 mL, 5.38 mmol), stirred at 25° C. for 16 hours, and partitioned with 10% Na2CO3. The aqueous phase was extracted with additional dichloromethane. The combined organic phase was dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-25% methyl tert-butyl ether/dichloromethane to give the title compound (1.33 g, 70% yield).

Workup

custompartitioned with 10% Na2CO3
extractionThe aqueous phase was extracted with additional dichloromethane
dry with materialThe combined organic phase was dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was chromatographed on silica gel eluting with 0-25% methyl tert-butyl ether/dichloromethane

Sources & evidence

ORD record: ord-184b1d8f8b034f7eb9feaa907baa20ab
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834043B2

Reaction notes

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