Trifluoroacetic acid → HCID 66875521, compound

HRID 2079781Notes

Reaction equation

HRID 2079781 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([NH:14][CH:15]1[CH:20]2[CH:16]1[CH2:17][N:18](C(OC(C)(C)C)=O)[CH2:19]2)(=[O:13])=[O:12].[C:28]([OH:34])([C:30]([F:33])([F:32])[F:31])=[O:29]>C(Cl)Cl>[F:31][C:30]([F:33])([F:32])[C:28]([OH:34])=[O:29].[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([NH:14][CH:15]1[CH:20]2[CH:16]1[CH2:17][NH:18][CH2:19]2)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59367631HCID 59367631, compound

Product 1

HCID 66875521HCID 66875521, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 6-[(2-napthylsulfonyl)amino]-3-azabicyclo[3.1.0]hexane-3-carboxylate (27.50 g, 68.43 mmol) in 20% TFA in DCM (300 ml) was stirred at r.t. for 2 h. The reaction mixture was concentrated in vacuo and then DCM (100 ml) was added and removed in vacuo three times to remove excess TFA giving the title compound as the trifluoroacetate salt (crude yield=34.0 g). This product was used in the next step without further purification. 1H NMR (400 MHz, d6-DMSO) δ: 1.86 (2H, s), 2.20 (1H, m), 3.22 (4H, m), 7.70-7.75 (2H, m), 7.83 (1H, dd), 8.08 (1H, d), 8.18-8.23 (3H, m), 8.33 (1H, br s), 8.48 (1H, s), 9.20 (1H, br s).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionDCM (100 ml) was added
  3. customremoved in vacuo three times
  4. customto remove excess TFA giving the title compound as the trifluoroacetate salt (crude yield=34.0 g)
  5. customThis product was used in the next step without further purification

Sources & evidence

ORD record
ord-ececa0287a074b35837baf71a9184447
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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