Trifluoroacetic acid → N-((7-Amino-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-yl)methyl)cyclobutanesulfonamide

HRID 82871Notes

Reaction equation

HRID 82871 reaction equation
[CH2:1]([CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][NH:19][S:20]([CH2:23][CH:24]3[CH2:26][CH2:25]3)(=[O:22])=[O:21])[CH:16]=2)[CH2:11][CH2:10][CH:9]1[NH:27]C(=O)OC(C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:27][CH:9]1[CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:17]2[CH:16]=[C:15]([CH2:18][NH:19][S:20]([CH:23]3[CH2:25][CH2:26][CH2:24]3)(=[O:22])=[O:21])[CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86685686tert-Butyl 1-benzyl-7-((cyclopropylmethylsulfonamido)methyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate

Product 1

HCID 46870540N-((7-Amino-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-yl)methyl)cyclobutanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 1-benzyl-7-((cyclopropylmethylsulfonamido)methyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (0.602 g, 1.242 mmol) was dissolved in dichloromethane (5 mL) and trifluoroacetic acid (0.5 mL, 6.49 mmol) and stirred overnight at room temperature. The solution was evaporated and partitioned between saturated aqueous NaHCO3 and ethyl acetate. Water was extracted with ethyl acetate (2×30 mL). The collected organic extracts were dried on MgSO4 and evaporated under reduced pressure to give a brown oil. Product was obtained as a brown oil (0.470 g, 1.22, 98%).

Workup

  1. customThe solution was evaporated
  2. custompartitioned between saturated aqueous NaHCO3 and ethyl acetate
  3. extractionWater was extracted with ethyl acetate (2×30 mL)
  4. customThe collected organic extracts were dried on MgSO4
  5. customevaporated under reduced pressure
  6. customto give a brown oil
  7. customProduct was obtained as a brown oil (0.470 g, 1.22, 98%)

Sources & evidence

ORD record
ord-954704e9dd5849fa8100e1310a85115c
Source dataset
uspto-grants-2014_09
Patent number
US08846741B2

Reaction notes

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