Sec-Butylamine → HCID 53234533, compound

HRID 1256120Notes

Reaction equation

HRID 1256120 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](O)=[O:10])[CH:7]=1.[CH:26]([NH2:30])([CH2:28][CH3:29])[CH3:27].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:24])(=[O:25])[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][CH:26]([CH2:28][CH3:29])[CH3:27])=[O:10])[CH:7]=1

Participants

7

Reactant 3

HCID 24874Sec-ButylamineHCID 2724699PyBOPHCID 53234452HCID 53234452, compound

Product 1

HCID 53234533HCID 53234533, compoundYield 13%

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 sec-butylamine (0.7 mL, 7 mmol) in 20 mL of DMF was added PyBOP (1550 mg, 3 mmol) and TEA (3 mL, 15 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 first purified by preparative HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column) followed by ISCO CombiFlash Rf silica chromatography eluted with 88:10:2 chloroform:MeOH:H2O to give the desired product as a yellow solid (100 mg, yield 13%). MS calcd for (C19H24BN3O5S): 417.2. MS found (ESI negative): (M−H)−=416.4. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.90 (s, 1H), 9.17 (s, 1H), 7.84 (d, J=8 Hz, 1H), 7.44 (d, J=2 Hz, 1H), 7.40 (d, J=8.8 Hz, 1H), 7.22 (d, J=8 Hz, 1H), 7.10 (dd, J=8.4, 2 Hz, 1H), 6.48 (d, J=2.4 Hz, 1H), 6.34 (dd, J=8.8, 2.4 Hz, 1H), 5.93 (bs, 2H), 4.87 (s, 2H), 3.78 (s, 2H), 3.71 (m, 1H), 1.40 (m, 2H), 1.05 (d, J=6.4 Hz, 3H), 0.82 (t, J=7.2 Hz, 3H).

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 first purified by preparative HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column)
  6. washeluted with 88:10:2 chloroform

Sources & evidence

ORD record
ord-b56569c50dd74fa5b367de6ff42b8bc9
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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