Trifluoroacetic acid → HCID 131727595, compound

HRID 2246495Notes

Reaction equation

HRID 2246495 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C@:15]2([O:24][C@H:23]([CH2:25][OH:26])[C@@H:21]([OH:22])[C@H:19]([OH:20])[C@H:17]2[OH:18])[OH:16])=[CH:11][C:10]=1[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH:35]2[CH2:40][CH2:39][N:38](C(OC(C)(C)C)=O)[CH2:37][CH2:36]2)=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.C(OCC)(=O)C>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C@:15]2([O:24][C@H:23]([CH2:25][OH:26])[C@@H:21]([OH:22])[C@H:19]([OH:20])[C@H:17]2[OH:18])[OH:16])=[CH:11][C:10]=1[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 131727596HCID 131727596, compound

Product 1

HCID 131727595HCID 131727595, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2 mL trifluoroacetic acid are added to a solution of 0.19 g 1-chloro-4-(β-D-glucopyranos-1-yl)-2-[4-(1-tert-butyloxycarbonylpiperidin-4-yloxy)-benzyl]-benzene in 4 mL dichloromethane. The solution is stirred for 1.5 h at ambient temperature and then diluted with ethyl acetate. The resulting solution is treated with aqueous potassium carbonate solution and the organic phase is separated. The remaining basic aqueous phase is extracted with ethyl acetate and the combined organic phases are dried over sodium sulfate. The solvent is removed under reduced pressure to yield the product.

Workup

  1. customthe organic phase is separated
  2. extractionThe remaining basic aqueous phase is extracted with ethyl acetate
  3. dry with materialthe combined organic phases are dried over sodium sulfate
  4. customThe solvent is removed under reduced pressure
  5. customto yield the product

Sources & evidence

ORD record
ord-b1150d1b98ce42fdb3e4b38be2fb64ff
Source dataset
uspto-grants-2010_03
Patent number
US07687469B2

Reaction notes

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