2483-48-9|(S)-Methyl 2,6-bis((tert-butoxycarbonyl)amino)hexanoate| Ambeed

CAS No. :	2483-48-9
Formula :	C₁₇H₃₂N₂O₆
M.W :	360.45
SMILES Code :	O=C(OC)[C@@H](NC(OC(C)(C)C)=O)CCCCNC(OC(C)(C)C)=O
MDL No. :	MFCD09952319
InChI Key :	WLPJOHSPBBUIQG-LBPRGKRZSA-N
Pubchem ID :	11078906

Safety of [ 2483-48-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 2483-48-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 2483-48-9 ]

[ 2483-48-9 ] Synthesis Path-Downstream 1~54

1
[ 908094-01-9 ]
[ 2483-46-7 ]
[ 2483-48-9 ]

References: [1]Journal of the American Chemical Society,1965,vol. 87,p. 611 - 619.

2
[ 2483-48-9 ]
[ 2592-20-3 ]

Yield	Reaction Conditions	Operation in experiment
2.5 g	With hydrazine hydrate; In methanol; at 20℃; for 5h;	Hydrazine hydrate (3.3 mL, 8.3 mmol) was added to a solution of compound lb (3.0 g, 8.3 mmol) in methanol (20 mL) and stirred at room temperature for 5 h. The completeness of the reaction was confirmed by TLC analysis. The volatiles were evaporated under reduced pressure and the residue obtained was partitioned between water and ethyl acetate. The organic layer was washed with water followed by brine solution. The separated organic layer was dried over Na2SO/t, filtered and evaporated to yield 2.5 g of compound lc. LCMS: 361.4 (M+H)+.

References: [1]Journal of the American Chemical Society,1965,vol. 87,p. 611 - 619.
[2]Journal of the American Chemical Society,2011,vol. 133,p. 462 - 477.
[3]Patent: WO2016/142852,2016,A1 .Location in patent: Paragraph 55.

3
[ 2483-48-9 ]
[ 97347-42-7 ]
[ 114659-55-1 ]

References: [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 2994 - 3001.

4
[ 687-64-9 ]
[ 24424-99-5 ]
[ 2483-48-9 ]

References: [1]Tetrahedron Asymmetry,1994,vol. 5,p. 1463 - 1464.
[2]Synlett,2002,p. 100 - 104.
[3]Journal of the American Chemical Society,2011,vol. 133,p. 462 - 477.

5
[ 2483-48-9 ]
[ 97347-42-7 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 2015 - 2020.
[2]Synthetic Communications,1996,vol. 26,p. 687 - 696.
[3]Synlett,2002,p. 100 - 104.
[4]Tetrahedron Asymmetry,1994,vol. 5,p. 1463 - 1464.

6
[ 24424-99-5 ]
lysine methyl ester dihydrochloride [ No CAS ]
[ 2483-48-9 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 2015 - 2020.
[2]Synthetic Communications,1996,vol. 26,p. 687 - 696.

7
[ 67-56-1 ]
[ 56-87-1 ]
[ 24424-99-5 ]
[ 2483-48-9 ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 5671 - 5674.
[2]Journal of Organic Chemistry,2008,vol. 73,p. 5180 - 5182.

8
[ 2483-48-9 ]
[ 97347-42-7 ]
[ 183890-50-8 ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 5671 - 5674.

9
[ 100-36-7 ]
[ 588719-15-7 ]
[ 2483-48-9 ]
2-(N,N-diethylamino)-N'-{3-[(N,N-dimethylaminophenyl)-4'-diazenyl]benzoyl}ethylamine [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2003,vol. 1,p. 1480 - 1485.

10
[ 2483-48-9 ]
[ 76-05-1 ]
L-lysine O-methyl ester bis-TFA salt [ No CAS ]

References: [1]Tetrahedron,2003,vol. 59,p. 5837 - 5848.

11
[ 2483-46-7 ]
[ 74-88-4 ]
[ 2483-48-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium carbonate; In ethyl acetate; N,N-dimethyl-formamide; at 10 - 20℃; for 5h;Inert atmosphere;	Example 2 Boc-L-Lys(Boc)-OMe A 1 L three-neck flask equipped with addition funnel, nitrogen inlet, thermometer and mechanical stirrer was charged with a solution of Boc-L-Lys(Boc)-OH (59.37 g, 161 mmol, 94 wt % in EtOAc) in N,N-dimethylformamide (anhydrous) (300 mL). Whilst stirring, potassium carbonate (24.5 g, 177 mmol) was added, and the resulting suspension was cooled on an ice bath to an internal temperature of +10 C. Iodomethane (34.3 g, 242 mmol, 15.04 mL) was added dropwise over 30 min via the addition funnel, while keeping the internal temperature <20 C. The ice bath was removed and the reaction mixture was allowed to reach room temperature. TLC indicated complete consumption of the starting material after 4.5 h of stirring at room temperature. All volatiles were removed in vacuo, the resulting white slurry solidified on standing, and it was stored at -20 C. overnight. The resultant material was taken up in water (1 L) and sat'd. NaHCO3 (0.5 L), and then extracted with EtOAc (3500 mL). The combined organic phases were washed with dilute brine (2200 mL), brine (2100 mL), then dried over Na2SO4 and concentrated. After stripping with heptane (2200 mL), the title compound was isolated as a white solid (57.08 g, 97% yield). 1H-NMR (CDCl3): In agreement with structure. LCMS (NQAD detection): Purity >99%, mass in agreement with molecular formula (pos. m/z=361 [M+1]+, 383 [M+Na]+). Specific rotation: [α]D22=6.38 (c=1.72, CHCl3).
3 g	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2h;	Potassium carbonate (1.8 g, 13.0 mmol) and methyl iodide (0.65 mL, 10.4 mmol) were added to a solution of compound la (3.0 g, 8.7 mmol) in DMF (25 mL) and stirred at room temperature for 2 h. The completeness of the reaction was confirmed by TLC analysis. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with water, brine, dried over Na2SC>4 and evaporated under reduced pressure to yield 3.0 g of compound lb. LCMS: 361.1 (M+H)+.

References: [1]Patent: US2016/376618,2016,A1 .Location in patent: Paragraph 0213-0218.
[2]Tetrahedron,2003,vol. 59,p. 5837 - 5848.
[3]Patent: WO2016/142852,2016,A1 .Location in patent: Paragraph 54.

12
[ 2483-48-9 ]
[ 183890-50-8 ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 3023 - 3025.

13
[ 2483-48-9 ]
(2S)-2-(N-tert-butoxycarbonyl-N-formylamino)pentanedioic acid 1-methyl ester [ No CAS ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 3023 - 3025.

14
[ 2483-48-9 ]
[ 934561-10-1 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 2015 - 2020.

15
[ 2483-48-9 ]
6-hydroxy-octahydro-quinolizin-4-one [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 2015 - 2020.

16
[ 2483-48-9 ]
[ 934561-11-2 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 2015 - 2020.

17
[ 2483-48-9 ]
[ 934561-12-3 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 2015 - 2020.

18
[ 2483-48-9 ]
1,2-(carbomethoxy)-(3,4,5,5a,6,7,8-heptahydro)pyrrolo[2,1,5-de]quinolizine [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 2015 - 2020.

19
[ 2483-48-9 ]
(-)-1-(carboethoxy)-2-ethyl-(3,4,5,5a,6,7,8-heptahydro)pyrrolo[2,1,5-de]quinolizine [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 2015 - 2020.

20
[ 2483-48-9 ]
[ 128726-47-6 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 2015 - 2020.
[2]Synlett,2002,p. 100 - 104.
[3]Synthetic Communications,1996,vol. 26,p. 687 - 696.
[4]Tetrahedron Asymmetry,1994,vol. 5,p. 1463 - 1464.

21
[ 2483-48-9 ]
[ 158414-69-8 ]

22
[ 2483-48-9 ]
[ 200184-53-8 ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 3023 - 3025.

23
[ 2483-48-9 ]
[ 227758-95-4 ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 3023 - 3025.

24
N-(benzyloxycarbonyl)lysine methyl ester hydrochloride [ No CAS ]
[ 2483-48-9 ]

References: [1]Organic and Biomolecular Chemistry,2003,vol. 1,p. 1480 - 1485.

25
[ 588719-10-2 ]
[ 2483-48-9 ]

References: [1]Organic and Biomolecular Chemistry,2003,vol. 1,p. 1480 - 1485.

26
[ 2483-48-9 ]
[ 174626-17-6 ]

References: [1]Synlett,2002,p. 100 - 104.

27
[ 2483-48-9 ]
[ 423157-47-5 ]

References: [1]Synlett,2002,p. 100 - 104.

28
[ 2483-48-9 ]
[ 423157-48-6 ]

References: [1]Synlett,2002,p. 100 - 104.

29
[ 2483-48-9 ]
[ 423157-51-1 ]

References: [1]Synlett,2002,p. 100 - 104.

30
[ 2483-48-9 ]
[ 423157-45-3 ]

References: [1]Synlett,2002,p. 100 - 104.

31
[ 2483-48-9 ]
[ 423157-49-7 ]

References: [1]Synlett,2002,p. 100 - 104.
[2]Synlett,2002,p. 100 - 104.

32
[ 2483-48-9 ]
[ 423157-46-4 ]

References: [1]Synlett,2002,p. 100 - 104.

33
[ 2483-48-9 ]
8-methoxy-3-(4-methoxybenzyloxymethyl)-2-(4-nitrobenzoyl)perhydro-1,6-isoquinolinedione [ No CAS ]

References: [1]Synlett,2002,p. 100 - 104.
[2]Synlett,2002,p. 100 - 104.

34
[ 2483-48-9 ]
[ 81505-49-9 ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 5671 - 5674.

35
[ 2483-48-9 ]
[ 213176-18-2 ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 5671 - 5674.

36
[ 2483-48-9 ]
(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-6-oxo-piperidin-2-ylmethyl ester [ No CAS ]

References: [1]Synthetic Communications,1996,vol. 26,p. 687 - 696.

37
[ 2483-48-9 ]
[ 158362-66-4 ]

References: [1]Tetrahedron Asymmetry,1994,vol. 5,p. 1463 - 1464.

38
[ 2483-48-9 ]
[ 158362-68-6 ]

References: [1]Tetrahedron Asymmetry,1994,vol. 5,p. 1463 - 1464.

39
[ 2483-48-9 ]
[ 158362-67-5 ]

References: [1]Tetrahedron Asymmetry,1994,vol. 5,p. 1463 - 1464.

40
[ 2483-48-9 ]
(3aS,5R,7aS,8aR)-2,3,5-Triphenyl-3a-phenylselanyl-hexahydro-1,6-dioxa-2,4a-diaza-s-indacen-4-one [ No CAS ]

References: [1]Tetrahedron Asymmetry,1994,vol. 5,p. 1463 - 1464.

41
[ 1070-19-5 ]
[ 2483-48-9 ]

References: [1]Journal of the American Chemical Society,1965,vol. 87,p. 611 - 619.

42
[ 10098-89-2 ]
[ 2483-48-9 ]

References: [1]Journal of the American Chemical Society,1965,vol. 87,p. 611 - 619.

43
[ 2483-48-9 ]
[ 139449-03-9 ]

References: [1]Journal of Organic Chemistry,2008,vol. 73,p. 5180 - 5182.

44
[ 24424-99-5 ]
[ 3017-32-1 ]
[ 2483-48-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 20℃; for 1h;	Step E1-1: Methyl N2,N6-bis(tert-butoxycarbonyl)-L-lysinate. To a solution of epsilon-Boc Lysine methyl ester 1 (35.9g, 121 mmol) suspended in the CH2CI2 (250 mL) and stirred at room temperature, was added Boc2θ, 99% (28.1 mL, 121 mmol) followed by careful addition of triethylamine, 99.5% (20.23 mL, 145 mmol). The solids dissolved and gentle gas evolotuion was noted. After 1 hr the reaction mixture was clear pale yellow with no noticable gas evoluiton. An aliquot was concentrated under N2- The reaction mixture was allowed to sit overnight at room temperature. Transfer to a sep funnel and wash with water (2 x 25OmL), NaHCO3 (50 mL 50% saturated), and brine. Dry over MgSO4 , filter and concentrate to an off white solid, wt 42 g. MS: M+Na = 383.

References: [1]Patent: WO2009/42093,2009,A1 .Location in patent: Page/Page column 97.

45
[ 2483-48-9 ]
[ 85535-55-3 ]

Yield	Reaction Conditions	Operation in experiment
		Step E1-2: Bis-Boc-Lysinol. To a solution of methyl 7V2,N6-bis(ter/-butoxycarbonyl)-L-lysinate (235g, 652 mmol) in the THF (2000 mL) cooled with an ice/water bath to 10C was added lithium borohydride, > 90% (22g, 1010 mmol) in portions over 45 minutes. After the addition was complete the reaction mixture was aged for 20 minutes then warmed to 50C for 1 hour. The reaction mixture was cooled to 0C and quenched by dropwise addition of MeOH (50 mL). After 15 minutes at 0C the bath was removed and 50 mL of 5N NaOH was added with 250 mL of brine. After 30 minutes of stirring at room temperature, the reaction mixture was diluted with 500 mL of water and partitioned. The aqueous layer was diluted with more water until the salts dissolved and was then extracted once with ether (500 mL). The combined organic layer was dried over Na2SO4. Ethyl acetate was added and the mixture was stirred at room temperature for15 minutes, filtered and concentrated to afford a colorless viscous oil. MS: M+Na = 355.
		EXAMPLE 1Preparation of N-[(5S)-5- { [(4-aminophenyl)sulfonyl](3-methylbutyl)amino}hydroxyhexyl]-Na-(metl oxycarbonyl)- -phenyl-L-phenylalaninamideStep 1 : preparation of tert-butyl {(25)-6-[(teri-butoxycarbonyl)amino]-l-hydroxyhexan-2- yl} carbamate; To a solution of methyl N^-(½ri-butoxycarbonyl)-L-lysmate hydrochloride(5.0 g, 16.85 mmol) and triethylamine (2.82 mL, 20.22 mol) in dic oromethane (84 mL) was added a solution of di-tert-butyl dicarbonaie (3.7 g, 1 .85 mmol) in dichloromethane(10 mL). The reaction mixture was stirred at room temperature overnight, poured into 10% HSO4, and extracted with dichloromethane (2X). The combined organics were washed with saturated aqueous aHC03, brine, dried over MgS04, filtered and concentrated to yield 6.1 g of methyl N^^-bis(tert-bntoxy ^b ny[)-L-lys atQ as an off white solid. MS'.M+Na = 383. The residue was dissolved in THF (85 mL), and the solution was cooled to 0C. 2 M of L1BH4 in THF (12.69 mL, 25.4 mmol) was slowly added. The reaction mixture was stirred at room temperature for 1 hour, then at 50 C for 1 hour. It was then cooled to 0C and methanol was carefully added (1.5 mL). The reaction temperature was allowed to stand at room temperature, and 1 N NaOH (2 mL) was added followed by the addition of brine. The reaction mixture was vigorously stirred at room temperature for 30 min, then extracted with EtOAc (2X). The combined organics were washed with brine, dried over gS04, filtered and concentrated to yield 5.8 g of bis-Boc-lysinol material as a colorless viscous oil. MS (M+Na) = 355.

References: [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 9579 - 9584.
[2]Patent: WO2009/42093,2009,A1 .Location in patent: Page/Page column 97-98.
[3]Patent: WO2012/55031,2012,A1 .Location in patent: Page/Page column 43-44.

46
[ 2483-48-9 ]
C₂₂H₄₁N₅O₅ [ No CAS ]