Trifluoroacetic acid → HCID 54747824, compound

HRID 2094767Notes

Reaction equation

HRID 2094767 reaction equation
[Br:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([C:14]([NH:16][CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])=[O:15])=[C:10]([OH:25])[C:9]3[CH2:26][S:27][CH2:28][C:8]2=3)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15])=[C:10]([OH:25])[C:9]3[CH2:26][S:27][CH2:28][C:8]2=3)=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86649740HCID 86649740, compound

Product 1

HCID 54747824HCID 54747824, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To tert-butyl N-{[1-(4-bromobenzyl)-4-hydroxy-2-oxo-1,2,5,7-tetrahydrothieno[3,4-b]pyridin-3-yl]carbonyl}glycinate (prepared in similar fashion to Reference Example 3 and the preceding Reference Examples, 1.007 g, 2.033 mmol) was added CH2Cl2 (10.0 mL) and TFA (2.0 mL) at rt. After 1 hr the reaction was heated to 40° C. for an additional 4 h. The reaction was concentrated and then diluted with Et2O and MeOH to crystallize the sample. The liquid was decanted away and the solid was washed twice with hexane to afford the title compound. HPLC/MS: 438.9.0 (M+1); Rt=3.38 min.

Workup

  1. customat rt
  2. concentrationThe reaction was concentrated
  3. additiondiluted with Et2O and MeOH
  4. customto crystallize the sample
  5. customThe liquid was decanted away
  6. washthe solid was washed twice with hexane

Sources & evidence

ORD record
ord-592a302255684e1bbc9a293e0d2c211a
Source dataset
uspto-grants-2013_05
Patent number
US08445680B2

Reaction notes

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