Isopropanol → HCID 67363825, compound

HRID 245696Notes

Reaction equation

HRID 245696 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([B:20]([OH:22])[OH:21])=[CH:16][C:15]=1[O:23][CH3:24].C(N(CC)[CH:29]([CH3:31])[CH3:30])(C)C.[CH3:34][CH:35]([OH:37])[CH3:36].O1C[CH2:41][CH2:40][CH2:39]1>O>[CH3:24][O:23][C:15]1[CH:16]=[C:17]([B:20]2[O:21][C:40]([CH3:41])([CH3:39])[C:29]([CH3:30])([CH3:31])[O:22]2)[CH:18]=[CH:19][C:14]=1[NH:13][C:5](=[O:11])[O:37][CH:35]([CH3:36])[CH3:34]

Participants

7

Reactant 5

HCID 3776Isopropanol2×HCID 8028Tetrahydrofuran3×HCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 57473274(4-Amino-3-methoxyphenyl)boronic acid

Product 1

HCID 67363825HCID 67363825, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of triphosgene (1.485 mmol, 0.441 g) in tetrahydrofuran (20 ml) was added drop wise a solution of 4-amino-3-methoxyphenylboronic acid, pinacol ester (4.01 mmol, 1 g) and N,N-diisopropylethylamine (5.02 mmol, 0.829 ml) in tetrahydrofuran (30 ml) at room temperature. The temperature was kept between 20 and 30° C. After 30 minutes a solution of 2-propanol (8.03 mmol, 0.614 ml) and N,N-diisopropylethylamine (5.02 mmol, 0.829 ml) in tetrahydrofuran (20 ml) was added drop wise to the reaction mixture keeping the temperature between the 20-30° C. The reaction mixture was heated till reflux. After two hours an additional 10 ml of 2-propanol was added and the reaction mixture stirred at reflux temperature for 3 days. The reaction mixture was poured in water (150 ml) and extracted with ethyl acetate (150 ml). The organic layer was washed with 10% sodium chloride solution (10 ml), dried (magnesium sulfate) and evaporated till dryness to yield isopropyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (1.18 g) as a dark brown oil

Workup

  1. customwas kept between 20 and 30° C
  2. custombetween the 20-30° C
  3. temperatureThe reaction mixture was heated
  4. temperaturetill reflux
  5. temperatureat reflux temperature for 3 days
  6. extractionextracted with ethyl acetate (150 ml)
  7. washThe organic layer was washed with 10% sodium chloride solution (10 ml)
  8. dry with materialdried (magnesium sulfate)
  9. customevaporated till dryness

Sources & evidence

ORD record
ord-797db83b34aa40af8a941aa05d5382e5
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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