Cesium carbonate → Methyl N-(tert-butoxycarbonyl)-4-(2-methylphenyl)-5-oxonorleucinate

HRID 1404487Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:12]([O:14][CH3:15])=[O:13])[CH2:10]I)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][C:30](=[O:32])[CH3:31]>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:12]([O:14][CH3:15])=[O:13])[CH2:10][CH:29]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[CH3:22])[C:30](=[O:32])[CH3:31])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of methyl N-(tert-butoxycarbonyl)-3-iodo-D-alaninate (1.58 g, 4.80 mmol) in DMF (24 mL) was added cesium carbonate (1.56 g, 4.80 mmol) and the mixture was stirred at 23° C. for 45 min. 1-(2-Methylphenyl)-propan-2-one (0.783 g, 5.28 mmol) and cesium carbonate (2.35 g, 7.20 mmol) were added and the resulting mixture was stirred for 18 h. The mixture was filtered and water was added to the filtrate. The mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with water (3×), brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (5% ethyl acetate→40% ethyl acetate/hexane) gave the title compound. MS: m/z=350.1 (M+1).

Workup

stirringthe resulting mixture was stirred for 18 h
filtrationThe mixture was filtered
additionwater was added to the filtrate
extractionThe mixture was extracted with ethyl acetate (3×)
washThe combined organic extracts were washed with water (3×), brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customPurification by silica gel chromatography (5% ethyl acetate→40% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-a0f47b80167a4c949cf380d85d522055
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912210B2

Reaction notes

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