Cesium carbonate → N-{5-chloro-2-(oxiran-2-ylmethoxy)-4-[(triisopropylsilyl)oxy]phenyl}-cyclopentanecarboxamide

HRID 270132Notes

Reaction equation

HRID 270132 reaction equation
[Cl:1][C:2]1[C:3]([O:17][Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])=[CH:4][C:5]([OH:16])=[C:6]([NH:8][C:9]([CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[N+](C1C=C(S(O[CH2:47][C@@H:48]2[CH2:50][O:49]2)(=O)=O)C=CC=1)([O-])=O>O1CCOCC1>[Cl:1][C:2]1[C:3]([O:17][Si:18]([CH:22]([CH3:24])[CH3:23])([CH:25]([CH3:27])[CH3:26])[CH:19]([CH3:20])[CH3:21])=[CH:4][C:5]([O:16][CH2:47][CH:48]2[CH2:50][O:49]2)=[C:6]([NH:8][C:9]([CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])[CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 68962023N-{5-chloro-2-hydroxy-4-[(triisopropylsilyl)oxy]phenyl}cyclopentanecarboxamide

Product 1

HCID 86601494N-{5-chloro-2-(oxiran-2-ylmethoxy)-4-[(triisopropylsilyl)oxy]phenyl}-cyclopentanecarboxamideYield 17.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-{5-chloro-2-hydroxy-4-[(triisopropylsilyl)oxy]phenyl}cyclopentanecarboxamide (140 mg, 0.3 mmol) was dissolved in 1,4-dioxane (20 mL). Caesium carbonate (170 mg, 0.5 mmol) was added, followed by (2S)-oxiran-2-y-methyl 3-nitrobenzenesulfonate (90 mg, 0.3 mmol). After stirring over night at room temperature the mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and concentrated. Purification by HPLC on C18 (Xterra, 5 um, 19×50 mm; acetonitrile/water 60/40 to 100/0 over 15 min) yielded 25 mg (17%) of the titled intermediate compound.

Workup

  1. customwas partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water
  3. concentrationconcentrated
  4. customPurification by HPLC on C18 (Xterra, 5 um, 19×50 mm; acetonitrile/water 60/40 to 100/0 over 15 min)

Sources & evidence

ORD record
ord-63fe470f8d1c45e3b81622d5120c734a
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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