Trifluoroacetic acid → HCID 23560792, compound

HRID 1058436Notes

Reaction equation

HRID 1058436 reaction equation
C([SiH](CC)CC)C.[CH3:8][O:9][C:10](=[O:51])/[C:11](/[NH:30][C:31](=[O:50])[C:32]1[CH:37]=[CH:36][C:35]([C:38]([NH:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([OH:48])[CH:43]=2)=[O:39])=[CH:34][C:33]=1[Cl:49])=[CH:12]/[C:13]1[S:17][C:16]([NH:18]C(OC(C)(C)C)=O)=[N:15][C:14]=1[C:26]([F:29])([F:28])[F:27].FC(F)(F)C(O)=O>ClCCl>[CH3:8][O:9][C:10](=[O:51])/[C:11](/[NH:30][C:31](=[O:50])[C:32]1[CH:37]=[CH:36][C:35]([C:38]([NH:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([OH:48])[CH:43]=2)=[O:39])=[CH:34][C:33]=1[Cl:49])=[CH:12]/[C:13]1[S:17][C:16]([NH2:18])=[N:15][C:14]=1[C:26]([F:29])([F:28])[F:27]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86586331HCID 86586331, compound

Product 1

HCID 23560792HCID 23560792, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylsilane (0.15 mL, 0.94 mmol) was added to a solution of (Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-[2-(1,1-dimethylethoxycarbonyl)amino-4-trifluoromethylthiazol-5-yl]propenoic acid methyl ester (130 mg, 0.198 mmol) in dichloromethane (1 mL). Trifluoroacetic acid (1 mL, 13.0 mmol) was added and the solution was stirred at room temperature for 2 h and then the solvents were removed under reduced pressure. NMR indicated that the reaction had not gone to completion, so the crude residue was re-dissolved in dichloromethane and treated with triethylsilane and trifluoroacetic acid as before. After the solution was stirred at room temperature for 3 h, the solvents were removed in vacuo and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was dried (Na2SO4), filtered and evaporated to give (Z)-3-(2-amino-4-trifluoromethylthiazol-5-yl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acid methyl ester (100 mg, 91% yield) as a yellow foam.

Workup

  1. customthe solvents were removed under reduced pressure
  2. dissolutionwas re-dissolved in dichloromethane
  3. additiontreated with triethylsilane and trifluoroacetic acid as before
  4. stirringAfter the solution was stirred at room temperature for 3 h
  5. customthe solvents were removed in vacuo
  6. customthe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  7. dry with materialThe organic phase was dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-801d5bafbadb4684b5de1a4f43ad16e8
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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