Trifluoroacetic acid → HCID 15166624, compound

HRID 1651188Notes

Reaction equation

HRID 1651188 reaction equation
[CH3:1][C:2]1[S:6][N:5]=[N:4][C:3]=1[S:7][CH2:8][C:9]1[CH2:16][S:15][C@H:14]2[N:11]([C:12](=[O:26])[C@H:13]2[NH:17][C:18](=[O:25])[CH2:19][C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)[C:10]=1[C:27]([O:29]C(C)(C)C)=[O:28].FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1.ClCCl>[CH3:1][C:2]1[S:6][N:5]=[N:4][C:3]=1[S:7][CH2:8][C:9]1[CH2:16][S:15][C@H:14]2[N:11]([C:12](=[O:26])[C@H:13]2[NH:17][C:18](=[O:25])[CH2:19][C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)[C:10]=1[C:27]([OH:29])=[O:28]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15166623HCID 15166623, compound

Product 1

HCID 15166624HCID 15166624, compoundYield 40.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

A cold (0° C.) solution of 2.62 g of the product of Example 7 in 20 ml of dry anisole and 25 ml of dichloromethane was treated with 20 ml of trifluoroacetic acid. After evaporation the residue was chromatographed as described in Example 7, giving 950 mg of the desired product. 'H NMR (300 MHz, CDCl3): δ 2.57 (s, 3H); 3.70 (AB quartet, 2H, 4-CH2); 3.87 (s, 2H); 4.17 (AB quartet, 2H, CH2S--); 4.97 (d, 1H, J=4.8 Hz, 6-H); 5.76 (dd, 1H, J=9.24 Hz, 4.8 Hz, 7-H); [6.98 (m, 2H) and 7.24 (m, 1H)(thienyl)].

Workup

  1. customAfter evaporation the residue
  2. customwas chromatographed

Sources & evidence

ORD record
ord-469ca00b2c354e02bec594b85e600dfc
Source dataset
uspto-grants-1990_05
Patent number
US04927922

Reaction notes

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