Trifluoroacetic acid → HCID 58975139, compound

HRID 737032Notes

Reaction equation

HRID 737032 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH2:15][CH:16]1[CH2:19][N:18]([C:20](=[O:45])[C:21]2[CH:26]=[CH:25][C:24]([S:27]([N:30]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:32]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[CH:31]3)(=[O:29])=[O:28])=[CH:23][CH:22]=2)[CH2:17]1)(C)(C)C>>[NH2:14][CH2:15][CH:16]1[CH2:17][N:18]([C:20]([C:21]2[CH:22]=[CH:23][C:24]([S:27]([N:30]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:32]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[CH:31]3)(=[O:29])=[O:28])=[CH:25][CH:26]=2)=[O:45])[CH2:19]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58975198HCID 58975198, compound

Product 1

HCID 58975139HCID 58975139, compoundYield 95.5%

Procedure

Add trifluoroacetic acid (5 mL) to [1-[4-(3-phenyl-indole-1-sulfonyl)-benzoyl]-azetidin-3-ylmethyl]-carbamic acid tert-butyl ester (853 mg, 1.56 mmol) causing much gas evolution. Rotary evaporate the reaction solution (40° C.; azeotroping 2× with MeOH). Dissolve the resultant yellow oil in MeOH (10 mL) and add hydroxide resin (Bio-Rad AG® 1-X8, 20-50 mesh; 5 g) to free-base the amine. Filter the mixture and rotary evaporate the filtrate (40° C.; azeotroped 3× with CH2Cl2) to yield 664 mg (95.3%) of (3-aminomethyl-azetidin-1-yl)-[4-(3-phenyl-indole-1-sulfonyl)-phenyl]-methanone as an off-white foam. MS (m/e): 446.02 (M+1).

Workup

  1. customRotary evaporate
  2. customthe reaction solution (40° C.; azeotroping 2× with MeOH)
  3. dissolutionDissolve the resultant yellow oil in MeOH (10 mL)
  4. additionadd hydroxide resin (Bio-Rad AG® 1-X8, 20-50 mesh; 5 g) to free-base the amine
  5. filtrationFilter the mixture
  6. customrotary evaporate
  7. customthe filtrate (40° C.; azeotroped 3× with CH2Cl2)

Sources & evidence

ORD record
ord-4c0b26c060e848f1b117b2cccf533ef0
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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