1-Iodopropane → Methyl 3-(hydroxymethyl)-5-[(methylsulfonyl)(propyl)amino]benzoate

HRID 899451Notes

Reaction equation

HRID 899451 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([N:14]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:15][CH2:16][CH3:17])[CH:13]=1)[C:8](O)=[O:9])=[O:4].NC1C=C(C(OC)=O)C=C(C=1)C(OC)=O.C(I)CC.B.C1COCC1>C1COCC1>[OH:9][CH2:8][C:7]1[CH:6]=[C:5]([CH:13]=[C:12]([N:14]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:15][CH2:16][CH3:17])[CH:11]=1)[C:3]([O:2][CH3:1])=[O:4]

Participants

6

Reactant 4

HCID 336431-IodopropaneHCID 66831Dimethyl 5-aminoisophthalateHCID 2723981Borane;tetrahydrofuranHCID 592118953-(Methoxycarbonyl)-5-[(methylsulfonyl)(propyl)amino]benzoic acid

Product 1

HCID 57775670Methyl 3-(hydroxymethyl)-5-[(methylsulfonyl)(propyl)amino]benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of: 3-(methoxycarbonyl)-5-[(methylsulfonyl)(propyl)amino]benzoic acid (12.0 g, 38.1 mmol, prepared from dimethyl 5-aminoisophthalate and propyl iodide using a similar procedure as described for the preparation of intermediate A) in THF (250 mL) cooled to 0° C. was added BH3-THF (190.3 mL, 190.3 mmol, 1 M in THF). After 10 min, the reaction mixture was allowed to warm to rt and stirred for 15 h. The reaction mixture was cooled back down to 0° C. and carefully quenched with MeOH. The mixture was concentrated to half its original volume and diluted with EtOAc and water. Following dilution, the organic layer was extracted, washed with sat. aq. NaHCO3 and brine, dried over sodium sulfate and concentrated in vacuo to provide methyl 3-(hydroxymethyl)-5-[(methylsulfonyl)(propyl)amino]benzoate as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.02 (s, 1H), 7.89 (s, 1H), 7.60 (s, 1H), 4.79 (d, J=5.7 Hz, 2H), 3.94 (s, 3H), 3.67 (t, J=7.2 Hz, 2H), 2.90 (s, 3H), 1.87 (br t, J=5.7 Hz, 1H), 1.55-1.45 (m, 2H), 0.92 (t, J=7.4 Hz, 3H).

Workup

  1. temperatureto warm to rt
  2. temperatureThe reaction mixture was cooled back down to 0° C.
  3. customcarefully quenched with MeOH
  4. concentrationThe mixture was concentrated to half its original volume
  5. additiondiluted with EtOAc and water
  6. extractionthe organic layer was extracted
  7. washwashed with sat. aq. NaHCO3 and brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6ea17aef918c43eb80b8652ea5ea6759
Source dataset
uspto-grants-2008_04
Patent number
US07354942B2

Reaction notes

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