Benzoyl chloride → HCID 11295723, compound

HRID 460406Notes

Reaction equation

HRID 460406 reaction equation
OC(C(F)(F)F)=O.[OH:8][CH:9]1[CH2:13][NH:12][CH2:11][CH:10]1[NH:14][C:15]([CH:17]([NH:29][C:30]([N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1)=[O:31])[CH2:18][S:19]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:21])=[O:20])=[O:16].C([O-])(O)=O.[Na+].[C:43](Cl)(=[O:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>O1CCOCC1>[C:43]([N:12]1[CH2:13][CH:9]([OH:8])[CH:10]([NH:14][C:15]([CH:17]([NH:29][C:30]([N:32]2[CH2:33][CH2:34][O:35][CH2:36][CH2:37]2)=[O:31])[CH2:18][S:19]([CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)(=[O:21])=[O:20])=[O:16])[CH2:11]1)(=[O:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 131726314HCID 131726314, compound

Product 1

HCID 11295723HCID 11295723, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Morpholine-4-carboxylic acid [1-(4-hydroxy-pyrrolidin-3-ylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amide TFA salt (215 mg, 0.39 mmol) was dissolved in 1,4-dioxane (20 mL). Saturated aqueous NaHCO3 solution (10 mL) was added followed by benzoyl chloride (0.2 mL, 1.72 mmol). The mixture was stirred at ambient temperature for 1 hour and then extracted with ethyl acetate. The combined organic layers were washed with saturated aqueous NaHCO3 and brine, dried with MgSO4 and evaporated under vacuum. The residue was purified by flash chromatography on silica gel (Eluent: 5% methanol in ethyl acetate to 20% methanol in ethyl acetate) to yield morpholine-4-carboxylic acid [1-(1-benzoyl-4-hydroxy-pyrrolidin-3-ylcarbamoyl)-2-phenylmethane-sulfonyl-ethyl]-amide (92mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with saturated aqueous NaHCO3 and brine
  3. dry with materialdried with MgSO4
  4. customevaporated under vacuum
  5. customThe residue was purified by flash chromatography on silica gel (Eluent: 5% methanol in ethyl acetate to 20% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-a41787bece5e4ee2b91b33aabd2b0f7b
Source dataset
uspto-grants-2007_03
Patent number
US07196099B2

Reaction notes

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