106825-79-0|(S)-3-Morpholinecarboxylic Acid| Ambeed

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Quality Control of [ 106825-79-0 ] Purity: 97% SDS Specification

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Product Details of [ 106825-79-0 ]

CAS No. :	106825-79-0
Formula :	C₅H₉NO₃
M.W :	131.12
SMILES Code :	O=C([C@H]1NCCOC1)O
MDL No. :	MFCD03426307
InChI Key :	JUNOWSHJELIDQP-BYPYZUCNSA-N
Pubchem ID :	1501894

Safety of [ 106825-79-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of [ 106825-79-0 ]

* 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 [ 106825-79-0 ]

[ 106825-79-0 ] Synthesis Path-Downstream 1~35

1
O-(2-chloroethyl)-L-serine [ No CAS ]
[ 106825-79-0 ]

References: [1]Bulletin of the Chemical Society of Japan,1987,vol. 60,p. 2963 - 2965.

2
[ 15219-97-3 ]
[ 106825-79-0 ]

References: [1]Tetrahedron Asymmetry,2006,vol. 17,p. 1775 - 1779.

3
[ 106825-78-9 ]
[ 106825-79-0 ]

References: [1]Bulletin of the Chemical Society of Japan,1987,vol. 60,p. 2963 - 2965.

4
[ 24424-99-5 ]
[ 106825-79-0 ]
[ 783350-37-8 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 1h;	INTERMEDIATE 33: MORPHOLINE-3 (S), 4-DICARBOXYLIC ACID 4- tert-butyl ester [00157] A suspension of morpholine-3 (S)-CARBOXYLIC acid (2.00 g, 15.3 mmol) in DMF (75 ml) was stirred at RT. Triethylamine (7.47 ml, 53.6 mmol) and di-tert-butyl dicarbonate (BOC20, 4.02 g, 18.4 mmol) were added. The suspension was stirred at RT for one hour, during which time the reaction formed a clear yellow solution. The solution was concentrated to a reduced volume (-25 ml) and diluted with water (15 ml) and IN HC1 (15 ml). The mixture was poured into a separatory funnel, diluted further with water (100 ml) and brine (100 ml), and extracted with ET20 (3 x 100 ml). The organic layer was washed with brine, dried, filtered and concentrated to yield a white solid. The solid, which contained excess BOC20, was dissolved in ET20 (500 ml) and extracted with IN NaOH (3 x 100 ml). The aqueous layer was acidified with 6N HC1 to approximately a pH of 2, then extracted quickly with ET20 (3 x 100 ml). The ET20 layer was dried, filtered and concentrated to yield white solid (3.07 g). H-NMR (300 MHz, DMSO-d6): 5 12.95 (br s, 1); 4.34-4. 30 (m, 1); 4.18-4. 10 (m, 1); 3.83-3. 74 (m, 1); 3.59-3. 51 (m, 2); 3.39-3. 32 (m, 1); 3.21-2. 95 (m, 1); 1.41-1. 36 (m, 9). NH40Ac standard conditions. ELSD Rf = 1.08 min. M-H = 230.
	With triethylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 1h;	Intermediate 33: morpholine-3(S), 4-dicarboxylic acid 4-tert-butyl ester A suspension of <strong>[106825-79-0]morpholine-3(S)-carboxylic acid</strong> (2.00 g, 15.3 mmol) in DMF (75 ml) was stirred at RT. Triethylamine (7.47 ml, 53.6 mmol) and di-tert-butyl dicarbonate (BOC2O, 4.02 g, 18.4 mmol) were added. The suspension was stirred at RT for one hour, during which time the reaction formed a clear yellow solution. The solution was concentrated to a reduced volume (25 ml) and diluted with water (15 ml) and 1N HCl (15 ml). The mixture was poured into a separatory funnel, diluted further with water (100 ml) and brine (100 ml), and extracted with Et2O (3100 ml). The organic layer was washed with brine, dried, filtered and concentrated to yield a white solid. The solid, which contained excess BOC2O, was dissolved in Et2O (500 ml) and extracted with 1N NaOH (3100 ml). The aqueous layer was acidified with 6N HCl to approximately a pH of 2, then extracted quickly with Et2O (3*100 ml). The Et2O layer was dried, filtered and concentrated to yield white solid (3.07 g). 1H-NMR (300 MHz, DMSO-d6): delta 12.95 (br s, 1); 4.34-4.30 (m, 1); 4.18-4.10 (m, 1); 3.83-3.74 (m, 1); 3.59-3.51 (m, 2); 3.39-3.32 (m, 1); 3.21-2.95 (m, 1); 1.41-1.36 (m, 9). NH4OAc standard conditions. ELSD Rf=1.08 min. M-H=230.
	With sodium hydrogencarbonate; In 1,4-dioxane; water; at 20℃; for 16h;	A mixture of (S)morphoine-3-carboxyic acid (1.0 g, 7.63 mmo) and Boc2O (1.77 m, 763 mmoD in 10% NaHCO3 so?ution in water (10 m, 7.63 mmofl and 1,4dioxane (10 m) was stirred at RT for 16h. Water and AcOEt were added to mixture and phases were separated. The aqueous ayer was acidified to pH 34 with IM aqueous citric acid (12 m) and extracted 3 times with AcOEt. The organic ayer was washed with brine, dried over a phase separator cartridge (ST), the sovent was evaporated and the residue dried under vacuum to afford (S)-4(tert-butoxycarbony)morphoHne-3-carboxyHc acid Mz = 232 [M+Hj+, Rt = 070 mm (UPLC Method B2), 1H NMR (400 MHz. DMSO-d5) 6ppm: 12.94 (bs, IH), 4.32 (dd, IH), 4.15 (dd, IH), 3.79 (ddd, IH), 3.58-3.51 (m, 2H), 3.39-2.97 (m, 2H), 1.38 (d, 9H).

References: [1]Patent: WO2004/92167,2004,A1 .Location in patent: Page 92.
[2]Patent: US2005/239781,2005,A1 .Location in patent: Page/Page column 94.
[3]Patent: WO2015/181747,2015,A1 .Location in patent: Page/Page column 53; 54.
[4]Patent: CN107793409,2018,A .Location in patent: Paragraph 0353; 0355.

5
[ 50-00-0 ]
[ 106825-79-0 ]
[ 1315051-74-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium hydroxide on carbon; In ethanol; at 20℃; for 24h;	EXAMPLE 19: 4-methyl-morpholine-3 (S) -carboxylic acid (6- CHLORO-9H-ss-CARBOLIN-8-YL)-AMIDE [00158] A slurry of morpholine-3 (S) -carboxylic acid (3.00 g, 22.9 mmol) in EtOH (115 ml) was stirred at RT. A solution of aqueous CH2O (3.42 ml, 45.8 mmol, 37% w/w in H20) was added, followed by Pd (OH) 2 (600 mg, 20% w/w on charcoal). The flask was charged with hydrogen (1 atm) and the grey slurry was stirred for 24 hr at RT under a balloon of hydrogen. The flask was purged with nitrogen and the black slurry was diluted with MeOH, filtered through filter paper and concentrated to a reduced volume. The pale grey solution was filtered through a 0.45 um syringe filter to remove residual Pd (OH) 2 and concentrated to yield a clear colorless oil. The oil was placed under high vacuum for 24 hr and a white, solid foam was isolated. The foam was dissolved in pyridine (200 ml) and 6-CHLORO-9H-P-CARBOLIN- 8-ylamine (3.74 g, 17.2 mmol) was added, followed by EDCI (5. 87 g, 30.6 mmol). The clear pale orange solution was stirred at RT for 24 hr. The solution was diluted with H20 (300 ml) and poured into a separatory funnel containing EtOAc (300 ml). The mixture was shaken and the layers were separated. The aqueous layer was extracted with EtOAc (3 x 150 ml) and the combined organic layers were washed with H2O and brine. The organic layer was dried, filtered and concentrated to yield a brown oil which was placed under high vacuum. The resulting brown foam was triturated with MeOH and the precipitate which formed was filtered and washed with MeOH. The resulting pale yellow solid was purified via chiral HPLC to yield a white solid (3.23 g). 1H-NMR (300 MHz, DMSO-d6): 5 11.36 (s, 1); 10.02 (s, 1) ; 9.04 (s, 1); 8.38 (d, 1); 8.22-8. 21 (m, 1); 8.15 (d, 1); 7.91-7. 90 (m, 1); 4.00 (dd, 1); 3.85-3. 81 (m, 1); 3.69 - 3. 58 (m, 2); 2.99-2. 95 (dd, 1); 2.89-2. 85 (m, 1); 2.32 (s, 3); 2.32-2. 24 (m, 1). NH40Ac standard conditions. DAD Rf = 1.89 min. M+H = 345. Chiral preparative HPLC: 10% v/v EtOH/Hexanes. Chiralcel OD column. Rf = 11.5-14 min. Enantiopurity of product 2 99% ee.
	With hydrogen;palladium(II) hydroxide/carbon; In ethanol; water; at 20℃; under 760.051 Torr; for 24h;	Example 19 4-methyl-<strong>[106825-79-0]morpholine-3(S)-carboxylic acid</strong> (6-chloro-9H-beta-carbolin-8-yl)-amide A slurry of <strong>[106825-79-0]morpholine-3(S)-carboxylic acid</strong> (3.00 g, 22.9 mmol) in EtOH (115 ml) was stirred at RT. A solution of aqueous CH2O (3.42 ml, 45.8 mmol, 37% w/w in H2O) was added, followed by Pd(OH)2 (600 mg, 20% w/w on charcoal). The flask was charged with hydrogen (1 atm) and the grey slurry was stirred for 24 hr at RT under a balloon of hydrogen. The flask was purged with nitrogen and the black slurry was diluted with MeOH, filtered through filter paper and concentrated to a reduced volume. The pale grey solution was filtered through a 0.45 mum syringe filter to remove residual Pd(OH)2 and concentrated to yield a clear colorless oil. The oil was placed under high vacuum for 24 hr and a white, solid foam was isolated. The foam was dissolved in pyridine (200 ml) and 6-chloro-9H-beta-carbolin-8-ylamine (3.74 g, 17.2 mmol) was added, followed by EDCI (5.87 g, 30.6 mmol). The clear pale orange solution was stirred at RT for 24 hr. The solution was diluted with H2O (300 ml) and poured into a separatory funnel containing EtOAc (300 ml). The mixture was shaken and the layers were separated. The aqueous layer was extracted with EtOAc (3*150 ml) and the combined organic layers were washed with H2O and brine. The organic layer was dried, filtered and concentrated to yield a brown oil which was placed under high vacuum. The resulting brown foam was triturated with MeOH and the precipitate which formed was filtered and washed with MeOH. The resulting pale yellow solid was purified via chiral HPLC to yield a white solid (3.23 g). 1H-NMR (300 MHz, DMSO-d6): delta 11.36 (s, 1); 10.02 (s, 1); 9.04 (s, 1); 8.38 (d, 1); 8.22-8.21 (m, 1); 8.15 (d, 1); 7.91-7.90 (m, 1); 4.00 (dd, 1); 3.85-3.81 (m, 1); 3.69-3.58 (m, 2); 2.99-2.95 (dd, 1); 2.89-2.85 (m, 1); 2.32 (s, 3); 2.32-2.24 (m, 1). NH4OAc standard conditions. DAD Rf=1.89 min. M+H=345. Chiral preparative HPLC: 10% v/v EtOH/Hexanes. Chiralcel OD column. Rf=11.5-14 min. Enantiopurity of product>=99% ee.

References: [1]Patent: WO2004/92167,2004,A1 .Location in patent: Page 93.
[2]Patent: US2005/239781,2005,A1 .Location in patent: Page/Page column 95.

6
[ 2052-49-5 ]
[ 106825-79-0 ]
[ 1233213-51-8 ]

References: [1]Tetrahedron Asymmetry,2010,vol. 21,p. 562 - 565.

7
[ 106825-79-0 ]
[ 1233213-46-1 ]

References: [1]Tetrahedron Asymmetry,2010,vol. 21,p. 562 - 565.

8
[ 106825-79-0 ]
[ 1233213-47-2 ]

References: [1]Tetrahedron Asymmetry,2010,vol. 21,p. 562 - 565.

9
[ 106825-79-0 ]
[ 1233213-48-3 ]

References: [1]Tetrahedron Asymmetry,2010,vol. 21,p. 562 - 565.

10
[ 106825-79-0 ]
[ 1233213-49-4 ]

References: [1]Tetrahedron Asymmetry,2010,vol. 21,p. 562 - 565.

11
[ 28920-43-6 ]
[ 106825-79-0 ]
[ 281655-37-6 ]

Yield	Reaction Conditions	Operation in experiment
		<strong>[106825-79-0](S)-<strong>[106825-79-0]morpholine-3-carboxylic acid</strong></strong> (2.00 g, 15.3 mmol) was added to dioxane (20 mL).Add potassium carbonate (5.50 g, 40.0 mmol) and stir at room temperature for 30 minutes.Subsequently, fluorenylmethoxycarbonyl chloride (6.54 g, 25.0 mmol) was added to the reaction system.After stirring at room temperature for 3 hours, the reaction was completed.Column chromatography (petroleum ether: ethyl acetate = 1:1) gave the title compound.

References: [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1111 - 1115.
[2]Patent: CN108440507,2018,A .Location in patent: Paragraph 0285; 0290; 0291; 0292.

12
[ 783350-37-8 ]
[ 106825-79-0 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid; In dichloromethane; at 20℃; for 0.5h;	(S)-4-(tert-Butoxycarbonyl)morpholine-3-carboxylic acid (4.60 g, 20.0 mmol)Add to dichloromethane (20 mL),Add trifluoroacetic acid (20 mL) and stir at room temperature.After 30 minutes, the reaction is completed.The reaction mixture was dried to give the title compound.

References: [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1111 - 1115.
[2]Patent: CN108440507,2018,A .Location in patent: Paragraph 0285; 0287; 0288; 0289.

13
[ 106825-79-0 ]
(S)-(9H-fluoren-9-yl)methyl-3-[{2-[{(tert-butoxycarbonyl)amino}methyl]-5-chlorobenzyl}carbamoyl]morpholine-4-carboxylate [ No CAS ]