85185-24-6|3-((tert-Butoxycarbonyl)amino)pentanedioic acid| Ambeed

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Quality Control of [ 85185-24-6 ] Purity: 97% SDS Specification

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Product Details of [ 85185-24-6 ]

CAS No. :	85185-24-6
Formula :	C₁₀H₁₇NO₆
M.W :	247.25
SMILES Code :	O=C(O)CC(NC(OC(C)(C)C)=O)CC(O)=O
MDL No. :	MFCD03002699
InChI Key :	WGYXEDFGBWPHCX-UHFFFAOYSA-N
Pubchem ID :	20480690

Safety of [ 85185-24-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 85185-24-6 ]

* 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.

Upstream synthesis route of [ 85185-24-6 ]
Downstream synthetic route of [ 85185-24-6 ]

[ 85185-24-6 ] Synthesis Path-Upstream 1~4

1
[ 1948-48-7 ]
[ 24424-99-5 ]
[ 85185-24-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydroxide In tetrahydrofuran; water at 20℃; for 120 h;	ss-GLUTAMIC acid (1.01 g, 6.8 MMOL) was dissolved in THF (30 ML) and water (15 ML). Di-tert- butyidicarbonate (2.98 g, 13.6 MMOL) and 10percent aqueous sodium hydroxide (8.3 ML) were added and the mixture was stirred at room temperature for 5 days. The mixture was evaporated and resuspended in water (30 ml), and then acidified with 1 M potassium hydrogen sulphate until pH=2. The aqueous phase was extracted with 2x 60 ml of ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered and evaporated to afford 1.5 g (90percent) of 3-tert-butoxycarbonylaminopentanedioic acid as white crystals. #x0;H-NMR (MeOD): 81. 43 (s; 9H); 2.55 (d; 4H); 4.25 (quin; 1H). HPLC-MS: (method B): m/z: 148 (M+1-Boc).

References: [1] Patent: WO2004/89362, 2004, A1, . Location in patent: Page/Page column 64.
[2] Asian Journal of Chemistry, 2014, vol. 26, # 15, p. 4716 - 4722.
[3] Chemistry Letters, 1988, # 10, p. 1643 - 1646.

2
[ 24424-99-5 ]
[ 85185-24-6 ]

References: [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 1, p. 69 - 74.

3
[ 120341-34-6 ]
[ 85185-24-6 ]

References: [1] Chemistry Letters, 1988, # 10, p. 1643 - 1646.

4
[ 628-48-8 ]
[ 85185-24-6 ]

References: [1] Asian Journal of Chemistry, 2014, vol. 26, # 15, p. 4716 - 4722.

[ 85185-24-6 ] Synthesis Path-Downstream 1~23

1
[ 1207-69-8 ]
[ 46460-73-5 ]
[ 85185-24-6 ]
[ 85185-22-4 ]

References: [1]Journal of the American Chemical Society,1983,vol. 105,p. 2913 - 2914.

2
[ 1948-48-7 ]
[ 24424-99-5 ]
[ 85185-24-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydroxide; In tetrahydrofuran; water; at 20℃; for 120h;	ss-GLUTAMIC acid (1.01 g, 6.8 MMOL) was dissolved in THF (30 ML) and water (15 ML). Di-tert- butyidicarbonate (2.98 g, 13.6 MMOL) and 10% aqueous sodium hydroxide (8.3 ML) were added and the mixture was stirred at room temperature for 5 days. The mixture was evaporated and resuspended in water (30 ml), and then acidified with 1 M potassium hydrogen sulphate until pH=2. The aqueous phase was extracted with 2x 60 ml of ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered and evaporated to afford 1.5 g (90%) of 3-tert-butoxycarbonylaminopentanedioic acid as white crystals. H-NMR (MeOD): 81. 43 (s; 9H); 2.55 (d; 4H); 4.25 (quin; 1H). HPLC-MS: (method B): m/z: 148 (M+1-Boc).

References: [1]Patent: WO2004/89362,2004,A1 .Location in patent: Page/Page column 64.
[2]Asian Journal of Chemistry,2014,vol. 26,p. 4716 - 4722.
[3]Chemistry Letters,1988,p. 1643 - 1646.

3
[ 24424-99-5 ]
3-aminoglutaric acid hydrochloride [ No CAS ]
[ 85185-24-6 ]

References: [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 69 - 74.

4
[ 46460-73-5 ]
[ 85185-24-6 ]
[ 98577-76-5 ]

References: [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 69 - 74.

5
[ 85185-24-6 ]
[ 85185-22-4 ]

References: [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 69 - 74.

6
[ 85185-24-6 ]
[ 98577-87-8 ]

References: [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 69 - 74.

7
[ 85185-24-6 ]
[ 98577-88-9 ]

References: [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 69 - 74.

8
[ 120341-34-6 ]
[ 85185-24-6 ]

References: [1]Chemistry Letters,1988,p. 1643 - 1646.

9
[ 204387-53-1 ]
[ 85185-24-6 ]
(+/-) 3-(1,5-di-(2-(S)-cyanopyrrolidin-1-yl)pentane)-1,5-dione carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%		() 3- (1,5-di-(2-(S)-Cyanopyrrolidin-1-yl)pentane-1, 5-dione carbamic acid tert-but ester 3-tert-Butoxycarbonylaminopentanedioic acid (0.10 g, 0.4 MMOL) was dissolved in DCM (9 ml) and DMF (1 ML). HOAT (0.11 G, 0.81 MMOL) and then EDAC (0.16 g, 0.81 MMOL) were added at 0C, and the reaction mixture was stirred for/2 hour at 0C. Pyrrolidine-2- (S)- carbonitrile (0.17 g, 0.81 MMOL) and DIEA (0.21 ml, 1.21 MMOL) were added and the mixture was slowly heated to room temperature, and stirred for 3 days. The reaction mixture was evaporated and dissolved in ethyl acetate (50 ml) and water 50 (ML). 1 M Potassium hydrogen sulphate (30 ML) was added until pH=2. The organic layer was isolated, and washed with water (10 ml), aqueous sodium hydrogen carbonate (10 ML), and brine (10 ml), and then dried over sodium sulphate, filtered and evaporated, and purified on preparative HPLC (Method A) to afford 85 mg (53%) of () 3- (1, 5-DI- (2- (S)-CYANOPYRROLIDIN-1-YL) PENTANE)-1, 5- dione carbamic acid ter-butyl ester as white crystals. HPLC-MS: (method B): m/z: 304 (M+1-Boc). Preparative HPLC (Method A): Rt= 9.08 min.

References: [1]Patent: WO2004/89362,2004,A1 .Location in patent: Page/Page column 65.

10
[ 628-48-8 ]
[ 85185-24-6 ]

References: [1]Asian Journal of Chemistry,2014,vol. 26,p. 4716 - 4722.

11
ammonium hydrogen trans-pent-2-ene-1,5-dioate [ No CAS ]
[ 85185-24-6 ]

References: [1]Asian Journal of Chemistry,2014,vol. 26,p. 4716 - 4722.

12
[ 85185-24-6 ]
[ 120341-34-6 ]

References: [1]Asian Journal of Chemistry,2014,vol. 26,p. 4716 - 4722.

13
[ 506-43-4 ]
[ 85185-24-6 ]
C₄₆H₈₁NO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%		Intermediate 12: Intermediate 11 (2.5 g, 10.11 mmol), EDC (5.8 g, 30.30 mmol), and DMAP (494 mg, 4.04 mmol) in an oven-dried flask (200 mE) with a magnetic bar was added anhydrous DCM (50 mE). The mixture was stirred at ambient temperature for 5 minutes to a clear solution. Einoleyl alcohol (6.5 g, 24.20 mmol) was then added and the mixture was stirred at room temperature overnight. The reaction was finally quenched with H20 (50 mE) and extracted with DCM twice (2x50 mE). Organic layers were combined, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure. The crude purified by flash chromatography purification system (80 g silica gel colunm) using a gradient of hexane for 2 mm, then 0-25% EtOAc/hexane for 15 mm, then 25% EtOAc/hexane for 5 mm, then 75% EtOAc/hexane for 5 mm under the flow rate at 60 mE/mm. The product fractions were collected and concentrated to yield Intermediate 12 (7.0 g, 93% yield) as a clear liquid. ?H mm (400 MHz, CDC13) oe: 5.38-5.3 1 (8H, m, CH=), 4.28 (1H, bs, NH), 4.08-4.05 (4H, m, OCH2), 2.78-2.75 (4H, m, rrrCHCH2CHrrr), 2.69-2.59 (4H, m, COCH2N), 2.06-2.02 (4H, m, CH2CH2CH), 1.62-1.58 (4H, m, CH2CH2O), 1.43 (9H, s, C(CH3)3), 1.35-1.26 (36H, m, CH2), 0.90-0.86 (6H, m, CH3).

References: [1]Patent: US2016/376229,2016,A1 .Location in patent: Paragraph 0561; 0563.

14
(R)-5-(benzyloxy)-3-((tert-butoxycarbonyl)amino)-5-oxo-pentanoic acid [ No CAS ]
[ 85185-24-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 2h;Inert atmosphere;	Intermediate 11: Boc-beta-H-Asp(OBz)-OH (35.0 g, 10.20 mmol) was dissolved in MeOH (45 mE) in a round-bottomed flask flushed with Argon gas. 10% Pd/C (350 mg) was added and the flask was flushed with Argon gas once again. Next, all air was removed via vacuum pump and a balloon filled with hydrogen gas was attached. Reaction mixture was allowed to stir for 2 hours at ambient temperature. The hydrogen balloon was removed and the mixture was then filtered out Pd/C catalyst through a pad of celite, followed by rinsing with copious amounts of MeOH. The filtrate was finally concentrated by a rotovap to yield Intermediate 11(2.5 g, 100% yield), which was used without further purification.

References: [1]Patent: US2016/376229,2016,A1 .Location in patent: Paragraph 0561; 0562.

15
[ 85185-24-6 ]
C₄₁H₇₃NO₄ [ No CAS ]