| Identification | More | [Name]
4-[(tert-Butoxycarbonylamino)methyl]benzoic acid | [CAS]
33233-67-9 | [Synonyms]
4-(BOC-AMINOMETHYL)BENZOIC ACID
4-(N-TERT-BUTOXYAMINOMETHYL)BENZOIC ACID
4-(TERT-BUTOXYCARBONYLAMINO-METHYL)-BENZOIC ACID
4-(TERT-BUTYLOXYCARBONYLAMINOMETHYL)-BENZOIC ACID
AKOS BBS-00000218
BOC-4-AMB-OH
BOC-(4)AMBZ-OH
BOC-(4-AMINOMETHYL)-BENZOIC ACID
BOC-AMB-OH
BOC-HN-CH2-PH(4)-COOH
BOC-PAMB
BOC-PAMB-OH
BOC-P-AMINOMETHYLBENZOIC ACID
N-T-BUTOXYCARBONYL-4-AMINOMETHYLBENZOIC ACID
4-(T-BUTYLOXYCARBONYLAMINOMETHYL)-BENZOIC ACID
N-tert-Butoxycarbonyl-4-(aminomethyl)-benzoic acid | [Molecular Formula]
C13H17NO4 | [MDL Number]
MFCD00228182 | [Molecular Weight]
251.28 | [MOL File]
33233-67-9.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29242990 |
| Hazard Information | Back Directory | [Chemical Properties]
white solid | [Uses]
4-(Boc-aminomethyl)benzoic Acid is the Boc protected form of 4-(Aminomethyl)benzoic Acid (A615230) and is used as a reagent in the synthesis of indoleamide derivatives as EP2 antagonists with high selectivity. 4-(Boc-aminomethyl)benzoic Acid is also used as a reagent in the synthesis of aminopyridine-derived amides as nicotinamide phosphoribosyltransferase inhibitors. | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
Phase 1 - Boc Protection: 4-(Aminomethyl)benzoic acid (10.00 g, 65.36 mmol) was stirred with di-tert-butyl dicarbonate (28.0 g, 130.72 mmol) in a solvent mixture of deionized water (100 mL) and tetrahydrofuran (100 mL) at room temperature. The reaction system was adjusted to pH ≈ 6 by slow addition of saturated aqueous sodium bicarbonate solution and the reaction was continuously stirred for 16 hours. Upon completion of the reaction, the reaction solution was carefully acidified to pH ≈ 3 with 1 M hydrochloric acid solution, at which time a white solid precipitated. The solid product was collected by filtration and washed with deionized water and dried to afford 4-[(tert-butoxycarbonylamino)methyl]benzoic acid as a white solid (16.1 g, 97% yield). Mass spectrometry analysis showed m/z = 274 [M + Na]+. | [References]
[1] Patent: WO2008/53131, 2008, A1. Location in patent: Page/Page column 58; 59-60
[2] Patent: WO2008/40934, 2008, A1. Location in patent: Page/Page column 57-58
[3] Patent: WO2010/20556, 2010, A1. Location in patent: Page/Page column 206
[4] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 965 - 984
[5] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 4, p. 501 - 508 |
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