Ethyl Acetate → 5-chloro-N-(((3S,3aS)-1-oxo-7-(2-aminosulfonylphenyl)-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)thiophene-2-carboxamide

HRID 1050223Notes

Reaction equation

HRID 1050223 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@H:11]2[C@H:19]3[N:14]([C:15]4[CH:23]=[CH:22][C:21]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=5[S:30]([NH:33]C(C)(C)C)(=[O:32])=[O:31])=[CH:20][C:16]=4[O:17][CH2:18]3)[C:13](=[O:38])[O:12]2)=[O:8])=[CH:4][CH:3]=1.CC(=O)OCC>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@H:11]2[C@H:19]3[N:14]([C:15]4[CH:23]=[CH:22][C:21]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=5[S:30]([NH2:33])(=[O:31])=[O:32])=[CH:20][C:16]=4[O:17][CH2:18]3)[C:13](=[O:38])[O:12]2)=[O:8])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 1185196015-chloro-N-(((3S,3aS)-1-oxo-7-(2-t-butylaminosulfonylphenyl)-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)thiophene-2-carboxamide

Product 1

HCID 1179870295-chloro-N-(((3S,3aS)-1-oxo-7-(2-aminosulfonylphenyl)-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)thiophene-2-carboxamideYield 81.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
40 °C

Procedure

Compound 5-chloro-N-(((3S,3aS)-1-oxo-7-(2-t-butylaminosulfonylphenyl)-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)thiophene-2-carboxamide (124 mg, 0.215 mmol) was dissolved in 2 ml of TFA. The resulting mixture was heated to 40° C. and agitated for 2 h. TLC (PE/EA=1/1) was employed to monitor the reaction. After the reaction completed, TFA was evaporated, and the remainder was diluted by 20 ml of EA, washed with 8 ml of water and 8 ml of saturated saline solution for one time each, dried over anhydrous sodium sulfate, and the solvent was evaporated. Column chromatography (PE/EA=2/1) afforded 91 mg of white solid, yield: 81.22%.

Workup

  1. customthe reaction
  2. customTFA was evaporated
  3. additionthe remainder was diluted by 20 ml of EA
  4. washwashed with 8 ml of water and 8 ml of saturated saline solution for one time each,
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b3c689bd53ac4f3e8db76ef77d6c92cc
Source dataset
uspto-grants-2016_07
Patent number
US09382265B2

Reaction notes

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