Trifluoroacetic acid → HCID 118093893, compound

HRID 1057017Notes

Reaction equation

HRID 1057017 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]1[CH:14]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]3[O:22][C:21]([CH2:23][NH:24]C(=O)OC(C)(C)C)=[N:20][C:19]=3[C:32]=2[O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:12]2[CH:40]=[CH:41][N:42]([S:43]([C:46]3[CH:51]=[CH:50][C:49]([CH3:52])=[CH:48][CH:47]=3)(=[O:45])=[O:44])[C:11]=2[C:10]1=[O:53]>C(Cl)Cl>[NH2:24][CH2:23][C:21]1[O:22][C:18]2[CH:17]=[CH:16][C:15]([C:13]3[C:12]4[CH:40]=[CH:41][N:42]([S:43]([C:46]5[CH:51]=[CH:50][C:49]([CH3:52])=[CH:48][CH:47]=5)(=[O:44])=[O:45])[C:11]=4[C:10](=[O:53])[N:9]([CH3:8])[CH:14]=3)=[C:32]([O:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:19]=2[N:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118103541HCID 118103541, compound

Product 1

HCID 118093893HCID 118093893, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2.20 mL) was added dropwise to a solution of tert-butyl [(5-{6-methyl-1-[(4-methylphenyl)sulfonyl]-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl}-4-phenoxy-1,3-benzoxazol-2-yl)methyl]carbamate (0.282 g, 0.440 mmol) in methylene chloride (2.20 mL) and the resultant reaction mixture was stirred at RT for 30 min. The reaction mixture was concentrated in vacuo to a residue that was dissolved in small amount of dichloromethane and added dropwise to a saturated solution of sodium bicarbonate at 0° C. The aqueous solution was extracted with dichloromethane to give the desired product (231 mg, 97%) which was used immediately without further purification. LCMS calculated for C29H25N4O5S (M+H)+: m/z=541.2. found: 541.1.

Workup

  1. customthe resultant reaction mixture
  2. concentrationThe reaction mixture was concentrated in vacuo to a residue that
  3. dissolutionwas dissolved in small amount of dichloromethane
  4. additionadded dropwise to a saturated solution of sodium bicarbonate at 0° C
  5. extractionThe aqueous solution was extracted with dichloromethane

Sources & evidence

ORD record
ord-32841682feaa479582625dda43906b7a
Source dataset
uspto-grants-2016_07
Patent number
US09399640B2

Reaction notes

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