Cesium carbonate → HCID 71655229, compound

HRID 270080Notes

Reaction equation

HRID 270080 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O.[CH:18]1([NH:21][C:22](=[O:50])[C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:25][C:24]=2[OH:49])[CH2:20][CH2:19]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH:18]1([NH:21][C:22](=[O:50])[C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)=[CH:25][C:24]=2[O:49][CH2:4][C@@H:2]2[CH2:3][O:1]2)[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 10796Cesium carbonate2×HCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 68960505HCID 68960505, compound

Product 1

HCID 71655229HCID 71655229, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (119 mg, 0.459 mmol), N-cyclopropyl-2-hydroxy-4-(trityloxy)benzamide (200 mg, 0.459 mmol) and cesium carbonate, Cs2CO3, (186.2 mg, 0.573 mmol) in dimethylformamide (3 mL) was kept on stirring at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulphate, Na2SO4, filtered, concentrated and the residue was purified by silica gel flash chromatography (0-40% ethyl acetate in petroleum ether) to give the subtitled compound (160 mg).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried over sodium sulphate, Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by silica gel flash chromatography (0-40% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-0b0ae58648bd4e92a86b03c4bc0d5932
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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