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

HRID 82868Notes

Reaction equation

HRID 82868 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][CH3:24])(=[O:22])=[O:21])[CH:16]=2)[CH2:11][CH2:10][CH:9]1[NH:25]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>[NH2:25][CH:9]1[CH:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:17]2[CH:16]=[C:15]([CH2:18][NH:19][S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86685683tert-Butyl 1-benzyl-7-(ethylsulfonamidomethyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate

Product 1

HCID 86685687N-((7-amino-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-yl)methyl)ethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 1-benzyl-7-(ethylsulfonamidomethyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (0.652 g, 1.422 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.

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

Sources & evidence

ORD record
ord-bf03f1b2e03f43f9a35be984d79be0cf
Source dataset
uspto-grants-2014_09
Patent number
US08846741B2

Reaction notes

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