Trifluoroacetic acid → HCID 59211968, compound

HRID 655183Notes

Reaction equation

HRID 655183 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.Br[C:9]1[CH:14]=[CH:13][C:12]([N:15]([C:32](=[O:41])/[CH:33]=[CH:34]/[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:16][C:17]([N:19]2[CH2:23][CH2:22][C@H:21]([NH:24]C(=O)OC(C)(C)C)[CH2:20]2)=[O:18])=[CH:11][CH:10]=1>ClCCl>[NH2:24][C@H:21]1[CH2:22][CH2:23][N:19]([C:17](=[O:18])[CH2:16][N:15]([C:12]2[CH:13]=[CH:14][C:9]([O:5][C:3]3[CH:2]=[CH:11][CH:10]=[CH:9][CH:14]=3)=[CH:10][CH:11]=2)[C:32](=[O:41])/[CH:33]=[CH:34]/[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:20]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59211949[(S)-1-(2-{(4-Bromophenyl)-[(E)-(3-phenylacryloyl)]amino}acetyl)pyrrolidin-3-yl]carbamic acid, tert-butyl ester

Product 1

HCID 59211968HCID 59211968, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (30 mL) was added to a solution of [(S)-1-(2-{(4-bromophenyl)-[(E)-(3-phenylacryloyl)]amino}acetyl)pyrrolidin-3-yl]carbamic acid, tert-butyl ester 3 (4.0 g, 7.57 mmol) in dichloromethane (90 mL). The reaction mixture was stirred at room temperature for 16 h, and then concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with 1M NaOH (×2), brine, dried (Na2SO4) and evaporated to give the title compound as a foam (2.78 g, 86%). 1HNMR (300 MHz) (d6-DMSO) δ 1.5-2.1 (2H, 4×m), 3.08 (1H, m), 3.1-3.6 (4H, m), 4.47, 4.50 (2H, 2×br s), 6.43 (1H, br d), 7.3-7.5 (7H, m), 7.53 (1H, d, J=16 Hz) and 7.65 (2H, d).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 1M NaOH (×2), brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-3a79e1887baa441a9e2f91a772cfce44
Source dataset
uspto-grants-2011_12
Patent number
US08071582B2

Reaction notes

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