Trifluoroacetic acid → HCID 22731904, compound

HRID 2083891Notes

Reaction equation

HRID 2083891 reaction equation
C([O:5][C:6](=[O:29])[CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][S:21][S:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)(C)(C)C.C(O)(C(F)(F)F)=O.[SiH](CC)(CC)CC>ClCCl.C1(C)C=CC=CC=1>[N:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[S:22][S:21][CH2:20][CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][C:6]([OH:29])=[O:5]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86590607HCID 86590607, compound

Product 1

HCID 22731904HCID 22731904, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 140 mg of 15-(2-pyridyldithio)-4,7,10,13-tetraoxapentadecanoic acid tert-butyl ester (13a) in 5 ml of dichloromethane was added 1.0 ml of TFA and 250 μl of Et3SiH. After stirring for 2 hrs, the mixture was diluted with 5 ml of toluene. The mixture was evaporated and then co-evaporated three times with 5 ml of toluene and dried under vacuum to yield of 122 mg (99% yield) of the title compound 14a (FIG. 7). 1H NMR (CDCl3) 13.331 (s, OH), 8.770 (d, 1H, J=5.4 Hz), 8.299 (t, 1H, J=7.7+7.7 Hz), 8.130 (d, 1H, J=8.2 Hz), 7.677 (t, 1H J=6.3+6.4 Hz), 3.703˜3.556 (m, 16H), 3.109 (t, 2H, J=6.4+6.4 Hz), 2.538 (t, 2H, J=6.1+6.1 Hz); 13C NMR 175.900, 157.402, 144.807, 129.114, 124.746, 123.635, 70.452, 70.327, 70.206, 70.184, 69.881, 69.862, 67.229, 66.407, 39.320, 34.866; MS 392.73 (M+H)+, 390.76 (M−H)−.

Workup

  1. customThe mixture was evaporated
  2. customdried under vacuum

Sources & evidence

ORD record
ord-c5860068cbfc47b3bca49d8b566dff45
Source dataset
uspto-grants-2004_04
Patent number
US06716821B2

Reaction notes

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