Trifluoroacetic acid → N-[2-amino-5-(2-thienyl)phenyl]-4-(2-methyl-2-oxido-1,2-oxaphospholan-5-yl)benzamide

HRID 1013545Notes

Reaction equation

HRID 1013545 reaction equation
[CH3:1][P:2]1(=[O:35])[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([NH:15][C:16]3[CH:21]=[C:20]([C:22]4[S:23][CH:24]=[CH:25][CH:26]=4)[CH:19]=[CH:18][C:17]=3[NH:27]C(=O)OC(C)(C)C)=[O:14])=[CH:9][CH:8]=2)[O:3]1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:27][C:17]1[CH:18]=[CH:19][C:20]([C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)=[CH:21][C:16]=1[NH:15][C:13](=[O:14])[C:10]1[CH:11]=[CH:12][C:7]([CH:4]2[O:3][P:2]([CH3:1])(=[O:35])[CH2:6][CH2:5]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 579260081,1-Dimethylethyl [2-({[4-(2-methyl-2-oxido-1,2-oxaphospholan-5-yl)phenyl]carbonyl}amino)-4-(2-thienyl)phenyl]carbamate

Product 1

HCID 57925867N-[2-amino-5-(2-thienyl)phenyl]-4-(2-methyl-2-oxido-1,2-oxaphospholan-5-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-dimethylethyl [2-({[4-(2-methyl-2-oxido-1,2-oxaphospholan-5-yl)phenyl]carbonyl}amino)-4-(2-thienyl)phenyl]carbamate (95 mg, 0.185 mmol) was taken up in DCM (5 mL)/TFA (2 mL). After 3 hours, saturated NaHCO3 was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo to give N-[2-amino-5-(2-thienyl)phenyl]-4-(2-methyl-2-oxido-1,2-oxaphospholan-5-yl)benzamide as a yellow solid. The title compound was obtained as a 1:1 mixture of diastereosiomers. MS: cal'd 413 (MH+), exp 413 (MH+).

Workup

  1. extractionthe products extracted into EtOAc (×2)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a25399b2bf684b989cb2eea6ebc9d3e8
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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