Trifluoroacetic acid → HCID 53246497, compound

HRID 1189576Notes

Reaction equation

HRID 1189576 reaction equation
[CH3:1][C:2]1[N:3]([CH2:35][C:36]([OH:38])=[O:37])[C:4]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:5]([CH:23](O)[C:24]([F:27])([F:26])[F:25])[C:6]=1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)(=[O:16])=[O:15].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[CH3:1][C:2]1[N:3]([CH2:35][C:36]([OH:38])=[O:37])[C:4]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:5]([CH2:23][C:24]([F:26])([F:27])[F:25])[C:6]=1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([N:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1)(=[O:15])=[O:16]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 67237437HCID 67237437, compound

Product 1

HCID 53246497HCID 53246497, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(2-methyl-3-(2-(morpholinosulfonyl)benzyl)-5-phenyl-4-(2,2,2-trifluoro-1-hydroxyethyl)-1H-pyrrol-1-yl)acetic acid (0.063 g, 0.114 mmol) was dissolved in 2 mL DCM and cooled to 0° C. 2,2,2-trifluoroacetic acid (1 ml, 0.114 mmol) was then added followed by triethylsilane (0.2 ml, 1.252 mmol). LC/MS shows reduction was instantly complete. The reaction mixture was directly concentrated to yield ˜5 mg of crude material, which was purified by preparative HPLC chromatography to give 18 mg (29.4%) of the desired material.

Workup

  1. concentrationThe reaction mixture was directly concentrated
  2. customto yield ˜5 mg of crude material, which
  3. customwas purified by preparative HPLC chromatography

Sources & evidence

ORD record
ord-de046d2aafc347ca8fd0d933c86eabfc
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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