Ammonia → HCID 67173384, compound

HRID 1256111Notes

Reaction equation

HRID 1256111 reaction equation
[F:1][C:2]1[C:11]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22]C(=O)C(F)(F)F)=[CH:18][C:17]=2[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])(=[O:15])=[O:14])=[CH:10][C:5]2[B:6]([OH:9])[O:7][CH2:8][C:4]=2[CH:3]=1.N>>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([S:13](=[O:14])(=[O:15])[NH:12][C:11]2[C:2]([F:1])=[CH:3][C:4]3[CH2:8][O:7][B:6]([OH:9])[C:5]=3[CH:10]=2)=[C:17]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:18]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 86655217HCID 86655217, compound

Product 1

HCID 67173384HCID 67173384, compoundYield 40%

Procedure

Ethyl 2-(2-(N-(5-fluoro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-5-(2,2,2-trifluoroacetamido)phenyl)acetate (0.25 g, 0.50 mmol) and NH3 (7M in MeOH, 5 mL) was heated to 80° C. for 2 hrs. The reaction was monitored by LC/MS. Purification: The solvent was removed in vacuo and the product was recrystallized from EtOAc/MeOH to give 80 mg of the title compound as a white solid (yield: 40%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.62 (s, 1H), 9.27 (bs, 1H), 7.64 (d, J=8.2 Hz, 1H), 7.31 (d, J=8.8 Hz, 1H), 7.16 (d, J=10 Hz, 1H), 6.41 (d, J=2.4 Hz, 1H), 6.36 (dd, J=8.8, 2 Hz, 1H), 5.94 (s, 2H), 4.88 (s, 2H), 4.05 (q, J=7.6 Hz, 2H), 3.87 (s, 2H), 1.17 (t, J=7.2 Hz, 3H); MS (ESI) m/z=407.1 (M−H, negative).

Workup

  1. customPurification
  2. customThe solvent was removed in vacuo
  3. customthe product was recrystallized from EtOAc/MeOH

Sources & evidence

ORD record
ord-32ca82dca01a4135aa315dcff2179443
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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