Water → Trifluoroacetic acid

HRID 733421Notes

Reaction equation

HRID 733421 reaction equation
C(OC([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][CH:11]([CH:16]1[C:29]3[CH:28]=[CH:27][C:26]([C:30](=[NH:36])[N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])=[CH:25][C:24]=3[O:23][C:22]3[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:12]2)=O)(C)(C)C.O.[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]>ClC(Cl)C>[CH:13]12[NH:8][CH:9]([CH2:15][CH2:14]1)[CH2:10][CH:11]([CH:16]1[C:29]3[CH:28]=[CH:27][C:26]([C:30]([N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])=[NH:36])=[CH:25][C:24]=3[O:23][C:22]3[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:12]2.[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]

Participants

6

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 57839231HCID 57839231, compound2×

Product 2

HCID 6422Trifluoroacetic acidHCID 11653974HCID 11653974, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To solution of crude 3-[3-(N,N-diethyl-carbamimidoyl)-9H-xanthen-9-yl]-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester, 3m (0.34 g) in dichloroethane (2 mL) was added H2O (0.1 mL) and TFA (2 mL). The mixture was stirred at rt for 1 h and evaporated. The residue was purified via reverse phase HPLC (eluent: CH3CN in water containing 0.1% TFA), yielding 0.263 g (56%) for two steps) of 9-(8-aza-bicyclo[3.2.1]oct-3-yl)-N,N-diethyl-9H-xanthene-3-carboxamidine, 4m as a TFA salt (MS m/z (MH+) 390.3.

Workup

  1. customevaporated
  2. customThe residue was purified via reverse phase HPLC (eluent: CH3CN in water containing 0.1% TFA)

Sources & evidence

ORD record
ord-d9dca0d0162a4729a6a5cfc51ecad74a
Source dataset
uspto-grants-2009_09
Patent number
US07589104B2

Reaction notes

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