p-Toluenesulfonic acid → HCID 89515272, compound

HRID 1778567Notes

Reaction equation

HRID 1778567 reaction equation
[C:1]([NH:4][C:5]([CH:26]1[CH2:29][C:28](OC)([O:30]C)[CH2:27]1)([CH2:13][CH2:14][CH2:15][CH2:16][B:17]1[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]1)[C:6]([NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.C1C=CC=CC=1.CCCCCCC>[C:1]([NH:4][C:5]([CH:26]1[CH2:29][C:28](=[O:30])[CH2:27]1)([CH2:13][CH2:14][CH2:15][CH2:16][B:17]1[O:21][C:20]([CH3:22])([CH3:23])[C:19]([CH3:25])([CH3:24])[O:18]1)[C:6]([NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 89515357HCID 89515357, compound

Product 1

HCID 89515272HCID 89515272, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 241BenzeneSolventHCID 8900HeptaneSolvent

Procedure

2-Acetamido-N-tert-butyl-2-(3,3-dimethoxycyclobutyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanamide (5.21 g, 11.10 mmol) was dissolved in acetone (110 mL) and treated with p-toluenesulfonic acid (106 mg, 0.56 mmol). The reaction was stirred overnight at room temperature, then diluted with benzene (500 mL) and heptane (250 mL), washed successively with water and saturated aqueous sodium chloride, dried over MgSO4, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 50-75% ethyl acetate in heptane to afford the desired product (3.40 g, 73%). Rf 0.31 (75% ethyl acetate in heptane). 1H NMR (CDCl3, 300 MHz) δ 6.83 (br s, 1H), 5.84 (br s, 1H), 3.45-3.33 (m, 1H), 3.09-2.82 (m, 6H), 2.02 (s, 3H), 1.54-1.05 (m, 25H), 0.77 (t, J=7.4 Hz, 2H). ESI MS found for C22H39BN2O5 m/z [423.1 (M+1)].

Workup

  1. washwashed successively with water and saturated aqueous sodium chloride
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with 50-75% ethyl acetate in heptane

Sources & evidence

ORD record
ord-01bc297ec8c64a88b6a40d3008fbd57d
Source dataset
uspto-grants-2016_02
Patent number
US09266908B2

Reaction notes

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