Ammonia → HCID 67174934, compound

HRID 1256110Notes

Reaction equation

HRID 1256110 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([NH:11][S:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21]C(=O)C(F)(F)F)=[CH:17][C:16]=3[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])(=[O:14])=[O:13])[CH:9]=[CH:10][C:5]=2[CH2:4][O:3]1.N>>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([S:12](=[O:13])(=[O:14])[NH:11][C:8]2[CH:9]=[CH:10][C:5]3[CH2:4][O:3][B:2]([OH:1])[C:6]=3[CH:7]=2)=[C:16]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:17]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 53234455HCID 53234455, compound

Product 1

HCID 67174934HCID 67174934, compoundYield 54%

Procedure

Ethyl 2-(2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-5-(2,2,2-trifluoroacetamido)phenyl)acetate (0.45 g, 0.92 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 194 mg of the title compound as a white solid (yield: 54%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.88 (s, 1H), 9.17 (bs, 1H), 7.48 (d, J=9.2 Hz, 1H), 7.41 (d, J=0.9 Hz, 1H), 7.21 (d, J=8 Hz, 1H), 7.10 (dd, J=8.4, 2 Hz, 1H), 6.41 (m, 2H), 5.93 (s, 2H), 4.86 (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=389.1 (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-7236f011d6294712b062860848cb7b50
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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