3-Hydroxybenzaldehyde → HCID 67443282, compound

HRID 1666287Notes

Reaction equation

HRID 1666287 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.FC(F)(F)C(O)=O.[CH3:17][O:18][C:19](=[O:32])[CH:20]([NH2:31])[CH2:21][C:22]1[C:23]2[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=2[S:25][CH:26]=1>C1(C)C=CC=CC=1>[CH3:17][O:18][C:19]([C@@H:20]1[NH:31][C@H:5]([C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([OH:1])[CH:3]=2)[C:26]2[S:25][C:24]3[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=3[C:22]=2[CH2:21]1)=[O:32]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 6422Trifluoroacetic acidHCID 13851855HCID 13851855, compound2×

Product 1

HCID 67443282HCID 67443282, compoundYield 122.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

1.45 g (11.9 mmol) of 3-hydroxy benzaldehyde and 4.2 ml (54.6 mmol) of trifluoro acetic acid are added to a solution of 2.04 g (8.7 mmol) of 2-amino-3-benzo[b]thiophen-3-yl-propionic acid methyl ester (compound B1) in 20 ml of toluene. The solution is stirred at 40° C. over night. The mixture is washed with a saturated solution of sodium hydrogen carbonate. The aqueous layer is washed with ethyl acetate and the combined organic layers are washed with 5 M hydrochloric acid and dried with magnesium sulfate. 3.61 g of a brown oil are obtained as the crude product.

Workup

  1. washThe mixture is washed with a saturated solution of sodium hydrogen carbonate
  2. washThe aqueous layer is washed with ethyl acetate
  3. washthe combined organic layers are washed with 5 M hydrochloric acid
  4. dry with materialdried with magnesium sulfate

Sources & evidence

ORD record
ord-cf76b4f75a884de781dc10cb945458fa
Source dataset
uspto-grants-2011_10
Patent number
US08044065B2

Reaction notes

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