Trifluoroacetic acid → HCID 90370190, compound

HRID 2176046Notes

Reaction equation

HRID 2176046 reaction equation
C([O:5][C:6](=[O:55])[C:7]([C:10]1[N:15]=[CH:14][C:13]([NH:16][C:17]([C:19]2[C:23]3[CH2:24][CH2:25][CH2:26][CH2:27][C:22]=3[S:21][C:20]=2[NH:28][C:29]([C:31]2[CH:32]=[C:33]([CH:52]=[CH:53][CH:54]=2)[CH2:34][N:35]([CH:47]([CH2:50][CH3:51])[CH2:48][CH3:49])[C:36](=[O:46])[CH2:37][CH2:38][C:39]([CH3:45])([CH3:44])[C:40]([O:42][CH3:43])=[O:41])=[O:30])=[O:18])=[CH:12][CH:11]=1)([CH3:9])[CH3:8])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:43][O:42][C:40](=[O:41])[C:39]([CH3:44])([CH3:45])[CH2:38][CH2:37][C:36]([N:35]([CH2:34][C:33]1[CH:32]=[C:31]([CH:54]=[CH:53][CH:52]=1)[C:29]([NH:28][C:20]1[S:21][C:22]2[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=2[C:19]=1[C:17]([NH:16][C:13]1[CH:12]=[CH:11][C:10]([C:7]([CH3:9])([CH3:8])[C:6]([OH:55])=[O:5])=[N:15][CH:14]=1)=[O:18])=[O:30])[CH:47]([CH2:48][CH3:49])[CH2:50][CH3:51])=[O:46]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90370271HCID 90370271, compound

Product 1

HCID 90370190HCID 90370190, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 675 mg of methyl 5-[{3-[(3-{[6-(1-tert-butoxy-2-methyl-1-oxopropan-2-yl)pyridin-3-yl]carbamoyl}-4,5,6,7-tetrahydro-1-benzothiophen-2-yl)carbamoyl]benzyl}(pentan-3-yl)amino]-2,2-dimethyl-5-oxopentanoate, 10 mL of methylene chloride, and 1.3 mL of TFA was stirred 15 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous sodium hydrogen carbonate solution was added to the residue, followed by extraction by using ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (10% methanol/chloroform), thereby obtaining 550 mg of 2-{5-[({2-[(3-{[(5-methoxy-4,4-dimethyl-5-oxopentanoyl)(pentan-3-yl)amino]methyl}benzoyl)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}carbonyl)amino]pyridin-2-yl}-2-methylpropanoic acid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona saturated aqueous sodium hydrogen carbonate solution was added to the residue
  3. extractionfollowed by extraction
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (10% methanol/chloroform)

Sources & evidence

ORD record
ord-dce72e6f251141fa8cf8ed609563399b
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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