Trifluoroacetic acid → HCID 59211968, compound

HRID 655182Notes

Reaction equation

HRID 655182 reaction equation
FC(F)(F)C(O)=O.[O:8]([C:15]1[CH:20]=[CH:19][C:18]([N:21]([C:38](=[O:47])/[CH:39]=[CH:40]/[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:22][C:23]([N:25]2[CH2:29][CH2:28][C@H:27]([NH:30]C(=O)OC(C)(C)C)[CH2:26]2)=[O:24])=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClCCl>[NH2:30][C@H:27]1[CH2:28][CH2:29][N:25]([C:23](=[O:24])[CH2:22][N:21]([C:18]2[CH:17]=[CH:16][C:15]([O:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[CH:20][CH:19]=2)[C:38](=[O:47])/[CH:39]=[CH:40]/[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:26]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59211991[(S)-1-(2-{(4-Phenoxyphenyl)-[(E)-(3-phenylacryloyl)]amino}acetyl)pyrrolidin-3-yl]carbamic acid, tert-butyl ester

Product 1

HCID 59211968HCID 59211968, compoundYield 20.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added to a solution of [(S)-1-(2-{(4-phenoxyphenyl)-[(E)-(3-phenylacryloyl)]amino}acetyl)pyrrolidin-3-yl]carbamic acid, tert-butyl ester 6 (60 mg) in dichloromethane (6 mL). The reaction mixture was stirred at room temperature for 30 min, and then concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with 1M NaOH, (×2), brine, dried (Na2SO4) and evaporated to dryness. The resultant residue was purified by column chromatography on silica gel, eluting with ethyl acetate/methanol/ammonium hydroxide (90:5:5) to give the title compound (10 mg). 1HNMR (300 MHz) (CDCl3) δ 1.6-2.3 (2H, m), 3.15-3.75 (5H, m), 4.40 (2H, m), 6.43 (1H, d, J=16 Hz), 7.02 (2H, d), 7.06 (2H, d), 7.15 (1H, t), 7.25-7.45 (9H, m) and 7.69 (1H, d, J=16 Hz).

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 to dryness
  6. customThe resultant residue was purified by column chromatography on silica gel
  7. washeluting with ethyl acetate/methanol/ammonium hydroxide (90:5:5)

Sources & evidence

ORD record
ord-9608cc454f004ecbbb6574edf0a6caab
Source dataset
uspto-grants-2011_12
Patent number
US08071582B2

Reaction notes

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