Citric Acid → HCID 53737916, compound

HRID 369452Notes

Reaction equation

HRID 369452 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C@@H:11]([O:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)=[O:17])[C@H:10]([NH:30][C:31](=[O:46])[C:32]2[CH:37]=[CH:36][C:35]([O:38][Si](C(C)(C)C)(C)C)=[CH:34][CH:33]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.O.O.O.[F-].[Cl-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C@@H:11]([O:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)=[O:17])[C@H:10]([NH:30][C:31](=[O:46])[C:32]2[CH:33]=[CH:34][C:35]([OH:38])=[CH:36][CH:37]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 5234Sodium ChlorideHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 53759693HCID 53759693, compound

Product 1

HCID 53737916HCID 53737916, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

754 mg of (3R,4R)-4-(Biphenyl-4-ylcarbonyloxy)-3-[4-(tert-butyl-dimethyl-silanyloxy)-benzoylamino]-azepane-1-carboxylic acid tert-butyl ester were dissolved in 10 ml tetrahydrofuran and 147 mg of tetrabutylammoniumfluoride trihydrate were added at 0° C. and the reaction mixture was stirred for two hours at room temperature. 2.5 ml of a saturated solution of sodium chloride and 2.5 ml of an aqueous 1 molar solution of citric acid were added. The organic layer was concentrated under vacuo diluted with ethyl acetate then washed with 5 ml of a saturated solution of sodium chloride dried over magnesium sulfate and evaporated. The crude compound was purified on silica gel (dichloromethane:ethylacetate 1:1) to yield 551 mg (89% yield) of (3R,4R)-4-(Biphenyl-4-ylcarbonyloxy)-3-(4-hydroxy-benzoylamino)-azepane-1-carboxylic acid tert-butyl ester.

Workup

  1. concentrationThe organic layer was concentrated under vacuo
  2. additiondiluted with ethyl acetate
  3. washthen washed with 5 ml of a saturated solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe crude compound was purified on silica gel (dichloromethane:ethylacetate 1:1)

Sources & evidence

ORD record
ord-5ca3d88c59ce421d936603b3b6eb6086
Source dataset
uspto-grants-2000_10
Patent number
US06136969

Reaction notes

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