101650-17-3| (S)-Methyl 2-amino-4-bromobutanoate| Ambeed

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CAS No. :	101650-17-3
Formula :	C₅H₁₀BrNO₂
M.W :	196.04
SMILES Code :	O=C(OC)[C@@H](N)CCBr
MDL No. :	MFCD03426290

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydrogencarbonate; at 20℃; for 20h;Inert atmosphere;	To a round bottom flask containing MeOH (7.5 mL) at 0C was added dropwise SOCl2 andstirred for 30 min. 3-Bromo-1-carboxypropan-1-aminium bromide was then added and themixture was stirred overnight. The crude ester was obtained upon evaporation of the reactionmixture, to which was then added Boc2O (342 mg, 1.57 mmol) and dioxane (5 mL). Themixture was cooled before dropwise addition of NaHCO3 (10%, 5 mL). The mixture wasstirred at rt for 20 h before extraction using DCM (2 x 20 mL). The crude was purified byflash column chromatography, product eluted at 45% EtOAc/hexanes as a colourless oil. Thecrude of ester 16 was taken on to subsequent reaction without further purification. 1H NMR(400 MHz, CDCl3) δ 5.12 (s, 1H), 4.48 - 4.37 (m, 1H), 3.42 (t, J = 7 Hz, 2H), 2.46 - 2.33 (m,1H), 2.20 (dq, J = 15, 7 Hz, 1H), 1.44 (s, 9H) ppm. To a round bottom flask charged with 16 (225 mg, 0.76 mmol) was added DMF (2.5 mL)followed by sodium azide (99 mg, 1.52 mmol), then heated to 80C for 22 h. The completionof the reaction was confirmed by proton NMR, then 2M NaOH (0.6 mL, 1.52 mmol) andMeOH (2 mL) were added to the reaction mixture and stirred at rt for 1 h. The reactionmixture was then adjusted to pH 5 using concentrated HCl and extracted using Et2O (3 x 30mL). The combined organic layers were washed with brine, dried over MgSO4 andconcentrated under reduced pressure to afford azido acid 17 as a colourless oil, (147 mg, 0.60mmol, 79%). The NMR spectra compares well with that reported in the literature [6]. 1HNMR (400 MHz, CDCl3) δ 5.22 (d, J = 13 Hz, 1H), 4.27 (bs, 1H), 3.38 (t, J = 7 Hz, 2H),2.14 - 2.02 (m, 1H), 1.90 (dq, J = 13, 7 Hz, 1H), 1.39 (s, 9H) ppm.
	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 6h;	4-Methoxybenzyl chloride (15.6g) was reacted with [2-AMINOETHANETHIOL] (7.7g) in methanol and sodium methoxide, to afford of [2- (4-METHOXYBEZYL-] sulfanyl) -ethylamine (1) (18. 8g). One half of this material was taken in [DICHLOROMETHANE] (cooling bath [0C).] Chloroacetyl chloride in the same solvent, was added slowly with stirring, followed by an equivalent of triethyl amine to produce 2-chloro [N- [2- (4-METHOXYBENZYL-SULFANYL)-ETHYL]] acetamide (2) in a 94% yield. Compound 2 was reacted with an equivalent amount of 1 in refluxing acetonitrile for 6 hrs to provide [N- [-2- (4-METHOXY-BENZYLSULFANYL)-ETHYL]-] [2- [2- (4-METHOXY-BENZYLSULFANYL)-ETHYLAMINO]-ACETAMIDE] (3) (40.4g). Compound 3 was reduced with lithium aluminium hydride (LAH) to yield 4 in 85%. To a cold solution of anhydrous methanol was added dropwise 10 equivalents of thionyl chloride so as to maintain the internal temperature below 10 [C.] Reaction mixture was further stirred for 1 hour and treated [WITHLO] g (L) -4-bromo-2-aminobutyric (5). The reaction was slowly warmed to room temperature (RT) over 1 hour and stirred at 40 C overnight. Volatiles were removed under reduced pressure to dryness, and residue triturated with dichloromethane (DCM) to afford an off white solid (12 g) (6). That solid was dissolved in tetrahydrofuran (THF), treated with 3 eq. diisopropyl ethyl amine (DIPEA) followed by dibutyl oxycarbonyl anhydride [(BOC2O).] The reaction was stirred at RT for 6 hours. The reaction mixture was diluted with ethyl acetate (100 mL) and the combined organics washed with saturated ammonium chloride (100 [ML),] brine (100 mL) and dried over sodium sulfate and filtered. The filtrate was concentrated to dryness to afford 11 [G] of [BUTYLOXYCARBONYL-2-AMINO-4-BROMOBUTYRIC] acid methyl ester (7) as a thick oil which slowly crystallized. Compound 7 was taken up in acetone (10 volumes) and treated with 5 equivalents of sodium iodide. The resulting yellowish solution was refluxed overnight. The reaction was then concentrated to dryness, the residue dissolved in water (150 mL) and extracted with DCM (150 mL). The organic layer was collected, washed with brine, dried and concentrated to dryness to provide 8 g of 8 as a pale oil, purity [OF 94%] (HPLC). 1.3 g of diamine 4 were treated with 2.4 g of iodide 8 in acetonitrile with DIPEA (3 eq) as the base. The reaction was then stirred at 70 [C] for 5 hours followed by further stirring at the same temperature overnight. After flash chromatography, Butyl [OXYCARBONYL-2-AMINO-4-F (2-F (BUTYL OXYCARBONYL] [ 3-AMINO-3-METHOXYCARBONYL-PROPYL)- [2- (4-METHOXY-BENZYLSULFANYL)-ETHYL]-AMINO] [}-ETHYL)- [2- (4-METHOXY-BENZYLSULFANYL)-ETHYL]-AMINO}-BUTYRIC] acid methyl ester (9) was obtained (40% yield). Treatment of 9 (0.9 g) with 10 equivalents [OF 4M HCL/DIOXANE] solution overnight afforded the dihydrochloride salt 10 in excellent purity and good yield. 5-Dimethylamino-l-naphthalenesulfonyl [(DANSYL)] linkage was achieved by reacting 10 with dansyl chloride and DIPEA to provide 0.9 g of 11 with a purity [OF >98%] after column chromatography. Hydrolysis of the esters was carried in a mixture of dioxane/water (2: 1) overnight to provide >95% conversion of the di-ester to [2-AMINO-4-F (2-F (3-AMINO-3-CARBOXY-PROPYL)- [2- (4-METHOXY-] [ BENZYLSULFANYL)-ETHYL]-AMINO}-ETHYL)- [2- (4-METHOXY-BENZYLSULFANYL)-ETHYL]-AMIN] [O}-BUTYRIC] acid [(THIOL-PROTECTED NST904).] At this point the reaction mixture was of a milky suspension and the mixture was diluted with water (10 mL) and the organic solvent removed [I7I] vacuo. The milky aqueous layer was then covered with ethyl acetate and acidified to pH 3.0 with 2.0 M HC1. The organic layer was collected, dried and concentrated to dryness to afford an off-white solid of thiol-protected NST904 (1.3 g) which was practically pure.'H NMR (300 MHz, [CDC13)] 8 8. 87 (d, J= 8.87 Hz, 2H), 8. 70 (d, [J=] 8.56 Hz, 2 H), 8. 40 (d, [J=7. 31HZ,] 2 H), 7.98 (d, [J=] 7. [63 HZ, 2 H),] 7.81 (m, [4 H),] 7.30 (d, J = 8.58 Hz, 2 H) 6. 87 (d, [J= 8. 62 HZ,] 2 H), 4.05 (dd, [J=] 3.91 Hz, [J=] 4.02 Hz, 2 H), 3.58 (bs, 4H), 3.3 (, s, 12 H), 3.29 (m, [10H),] 2.77 (m, 4H), 2.23 (m, 2H), 2.02 (m, 2H). Melting range (DSC); MS (ESI) [CALCD] [1088,] found 1089 (M+ 1). IR (KBr), 3442. [86,] 2950.0, 1729.97, 1612.46, 1516.32, 1462.91, 1331.16, 1252. [82,] 1145.99 [CM~L. HPLC] Hypersil BDS, C18 4.5 x 150 mm, [5) LI.] Solvent A: H20/0. [1% TFA,] solvent B Acetonitrile/0.1% TFA; gradient of 30% B to 100% B over 17.0 min, flow rate 1.0 mL/min, detector [&COMMAT; ] 254 nm, Rt 10.318 (94.0%).

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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H302	Harmful if swallowed
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H312	Harmful in contact with skin
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H320	Causes eye irritation
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H360	May damage fertility or the unborn child
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H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 101650-17-3

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CAS No.: 101650-17-3

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[ 101650-17-3 ] Synthesis Path-Downstream 1~1

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