Isobutylamine → HCID 67310372, compound

HRID 1256122Notes

Reaction equation

HRID 1256122 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:12](=[O:25])(=[O:24])[NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)=[C:6]([CH2:8][C:9]([OH:11])=O)[CH:7]=1.[CH2:26]([NH2:30])[CH:27]([CH3:29])[CH3:28].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C.O.CO>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:12](=[O:25])(=[O:24])[NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)=[C:6]([CH2:8][C:9]([NH:30][CH2:26][CH:27]([CH3:29])[CH3:28])=[O:11])[CH:7]=1

Participants

7

Reactant 3

HCID 6558IsobutylamineHCID 2724699PyBOPHCID 53234452HCID 53234452, compound

Product 1

HCID 67310372HCID 67310372, compoundYield 51.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(5-amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetic acid (720 mg, 2 mmol) and isobutylamine (1.2 mL, 12 mmol) in 20 mL of DMF was added PyBOP (1550 mg, 3 mmol) and TEA (1 mL, 7 mmol). The reaction mixture was stirred for 16 hours. After water was added, the reaction mixture was extracted with ethyl acetate and washed with water, 1N HCl and brine. The organic layer was dried over Na2SO4 and concentrated. The crude residue was purified by ISCO CombiFlash Rf silica chromatography eluted with 88:10:2 chloroform:MeOH:H2O to give the desired product as a yellow solid (430 mg, yield 51%). MS calcd for (C19H24BN3O5S): 417.2. MS found (ESI negative): (M−H)−=416.1. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.89 (s, 1H), 9.17 (bs, 1H), 7.96 (t, J=5.6 Hz, 1H), 7.41 (m, 2H), 7.22 (d, J=8.4 Hz, 1H), 7.10 (d, J=8 Hz, 1H), 6.47 (s, 1H), 6.34 (d, J=8 Hz, 1H), 5.93 (bs, 2H), 4.87 (s, 2H), 3.80 (s, 2H), 2.93 (t, J=6.4 Hz 2H), 1.72 (m, 1H), 0.85 (d, J=7.8 Hz, 6H).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with water, 1N HCl and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude residue was purified by ISCO CombiFlash Rf silica chromatography
  6. washeluted with 88:10:2 chloroform

Sources & evidence

ORD record
ord-0a4da9800cba405ba22b37e804b24d17
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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