Trifluoroacetic acid → HCID 25053962, compound

HRID 2423159Notes

Reaction equation

HRID 2423159 reaction equation
C([C:3]1[C:11]([O:12][CH2:13][C@H:14]([NH:16][C:17](=O)OC(C)(C)C)[CH3:15])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])=[O:25])=O.C(O)(C(F)(F)F)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:15][C@H:14]1[NH:16][CH2:17][C:3]2=[C:4]3[C:8](=[CH:9][CH:10]=[C:11]2[O:12][CH2:13]1)[N:7]([S:24]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)(=[O:25])=[O:26])[CH:6]=[CH:5]3

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 86621715HCID 86621715, compound2×

Product 1

HCID 25053962HCID 25053962, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl ((1R)-2-{[4-formyl-1-(phenylsulfonyl)-1H-indol-5-yl]oxy}-1-methylethyl)carbamate (Intermediate 19, 0.040 g, 0.087 mmol) was dissolved in DCM (2 mL) and TFA (0.5 mL) was added. The mixture was stirred for 1 hour at room temperature and evaporated. The residue was dissolved in THF (2 mL) and sodium triacetoxyborohydride (37.0 mg, 0.176 mmol) was added. The mixture was stirred for 1 hour, evaporated and purified by flash chromatography using 2.5%-5% MeOH in DCM as the eluent to give the title compound (25 mg) as a white solid. MS m/z 343 [M+H]+.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in THF (2 mL)
  3. stirringThe mixture was stirred for 1 hour
  4. customevaporated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-a111709a9d5643a0bcd0305914c6a5e2
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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