ChemicalBook CAS DataBase List BOC-3-AMINOBENZOIC ACID

BOC-3-AMINOBENZOIC ACID synthesis

11synthesis methods

Product Name:BOC-3-AMINOBENZOIC ACID
CAS Number:111331-82-9
Molecular formula:C12H15NO4
Molecular Weight:237.25

tert-butyl [3-(ethoxycarbonyl)phenyl]carbamate

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Yield: 86%

Reaction Conditions:

Stage #1:tert-butyl [3-(ethoxycarbonyl)phenyl]carbamate with lithium hydroxide;water in tetrahydrofuran;methanol at 20; for 16 h;
Stage #2: with hydrogenchloride in water

Steps:

27
The ester prepared in preparation 25 (750 mg, 2.83 mmol), lithium hydroxide (415 mg, 9.89 mmol), methanol (15 mL), water (15 mL), and tetrahydrofuran (45 mL), were combined in a 250 mL round bottomed flask, fitted with a stirbar, and under a nitrogen atmosphere. The mixture was stirred vigorously at room temperature for 16 hours, then was concentrated under vacuum, dissolved in 1N HCl, and extracted with methylene chloride (100 mL*3). Organic layer was dried (MgSO4), filtered, and concentrated under vacuum, yielding 600 mg of white solid. This material was purified by recrystallization in hexanes:ethyl acetate, yielding the title compound as 580 mg (86%) white solid.[0184] Electrospray-MS 238.0 (M*+1).

References:

Eli Lilly and Company US6639107, 2003, B1 Location in patent:Page/Page column 37

24424-99-5 Synthesis