[ CAS No. 89524-99-2 ] {[proInfo.proName]}

Name: 89524-99-2|Methyl 2-acetamido-2-(dimethoxyphosphoryl)acetate|97%
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Quality Control of [ 89524-99-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 89524-99-2 ]

CAS No. :	89524-99-2	MDL No. :	MFCD08443722
Formula :	C₇H₁₄NO₆P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MXNIODZSMNMILW-UHFFFAOYSA-N
M.W :	239.16	Pubchem ID :	11746707
Synonyms :

Safety of [ 89524-99-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H312-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 89524-99-2 ]

* 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 [ 89524-99-2 ]
Downstream synthetic route of [ 89524-99-2 ]

[ 89524-99-2 ] Synthesis Path-Upstream 1~10

1
[ 89524-99-2 ]
[ 643-79-8 ]
[ 27104-73-0 ]

Reference： [1] Tetrahedron Letters, 1999, vol. 40, # 45, p. 7935 - 7938

2
[ 108-24-7 ]
[ 100945-15-1 ]
[ 89524-99-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With hydrogen In methanol for 3 h;	C152 (12.65 g, 38. 2 mmol) and acetic anhydride (9.02 ML, 95.5 mmol) in MEOH (100 mL) are added to a Parr flask. The solution is hydrogenated with 10percent Pd/C catalyst (0.640 g) at 45 PSI for 3h. The catalyst is filtered off, and the filtrate is concentrated in vacuo to an oil. The oil is placed under reduced pressure and solidified as the reduced pressure is applied. The white residue is dissolved in a small amount of EtOAc and stirred vigorously while pentane is added until a precipitate began to form. The precipitate is removed by filtration to give methyl (acetylamino) (dimethoxyphosphoryl) acetate (C153 ! AS a white powder (87percent yield). MS (CI) for C7HL4NO6P, M/Z : 240 (M+H) +.

Reference： [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 8, p. 1277 - 1286
[2] Synthesis, 1984, # 1, p. 53 - 60
[3] Organic Syntheses, 2011, vol. 88, p. 152 - 161
[4] Tetrahedron, 2007, vol. 63, # 51, p. 12740 - 12746
[5] Patent: WO2004/39815, 2004, A2, . Location in patent: Page 52 - 53
[6] Journal fuer Praktische Chemie - Practical Applications and Applied Chemistry (Germany), 2000, vol. 342, # 8, p. 736 - 744
[7] Synlett, 2008, # 10, p. 1532 - 1536

3
[ 73198-56-8 ]
[ 121-45-9 ]
[ 89524-99-2 ]

Yield	Reaction Conditions	Operation in experiment
44%	Stage #1: With phosphorus trichloride In toluene at 70℃; for 17 h; Stage #2: at 70℃; for 2 h;	The phosphinyl compound 39 was prepared according to a procedure described by Schmidt et al.¹⁹⁷Phosphorus (III) chloride (3.91 mL, 44.6 mmol) was added to a solution of methyl N-acetyl-2-methoxyglycinate 43 (7.19 g, 44.6 mmol) in toluene (100 mL) at 70° C. and the mixture was stirred at this temperature for 17 h. Trimethyl phosphite (5.27 mL, 44.7 mmol) was then added dropwise and the reaction mixture was left to stir for 2 h at 70° C. The mixture was evaporated under reduced pressure and the resultant oil was re-dissolved in DCM (100 mL) and washed with saturated NaHCO₃solution (3.x.100 mL). The organic extract was dried (MgSO₄) and evaporated under reduced pressure to afford the product 39 as a colourless solid (1.46 g, 14percent). The combined aqueous layers were extracted in a continuous extractor with DCM (150 mL) for 3 days. The organic layer was then evaporated under reduced pressure to give the product 39 as a colourless solid (3.21 g, 30percent) (44percent combined yield), m.p. 89-91° C. (lit.¹⁹⁷88-89° C.). Spectroscopic data indicated the crude product 39 did not require purification and was used directly in the subsequent reaction (Section 7.94). ν_max(KBr): 3281m, 3050w, 2852w, 1749m, 1673m, 1540m, 1309m, 1287w, 1232w, 1133m, 1061m, 1028m cm^-1. ¹H n.m.r. (300 MHz, CDCl₃): δ 2.08 (s, 3H, CH₃CO), 3.80-3.85 (m, 9H, COOCH₃, 2.x.P-OCH₃), 5.23 (dd, J=22.2, 8.9 Hz, 1H, H2), 6.42 (d, J=8.8 Hz, 1H, NH). ¹³C n.m.r. (75 MHz, CDCl₃): δ 22.7 (CH₃CO), 50.0 (d, J=146.8 Hz, C2), 53.3 (COOCH₃), 54.1 (d, J=6.8 Hz, P-OCH₃), 54.2 (d, J=6.5 Hz, P-OCH₃), 167.0 (d, J=2.2 Hz, CONH), 169.0 (d, J=6.0 Hz, C1). Mass Spectrum (ESI⁺, MeOH): m/z 262.1 (M+Na)⁺, C₆H₁₁NNaO₄requires 262.2.

Reference： [1] Patent: US2007/197429, 2007, A1, . Location in patent: Page/Page column 56
[2] New Journal of Chemistry, 2003, vol. 27, # 2, p. 387 - 394
[3] Patent: US9102708, 2015, B2, . Location in patent: Page/Page column 19; 118; 119

4
[ 121-45-9 ]
[ 89524-99-2 ]

Reference： [1] Tetrahedron Letters, 2006, vol. 47, # 20, p. 3439 - 3442

5
[ 126484-84-2 ]
[ 121-45-9 ]
[ 89524-99-2 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995, # 12, p. 1603 - 1610
[2] Synlett, 2008, # 3, p. 402 - 404

6
[ 60-35-5 ]
[ 60190-78-5 ]
[ 89524-99-2 ]

Reference： [1] Synthesis, 2005, # 20, p. 3571 - 3580

7
[ 112051-97-5 ]
[ 89524-99-2 ]

Reference： [1] Synthetic Communications, 1990, vol. 20, # 22, p. 3395 - 3401

8
[ 112051-88-4 ]
[ 121-45-9 ]
[ 89524-99-2 ]

Reference： [1] Synthetic Communications, 1990, vol. 20, # 22, p. 3395 - 3401

9
[ 89537-21-3 ]
[ 89524-99-2 ]

Reference： [1] Tetrahedron Letters, 1989, vol. 30, # 38, p. 5121 - 5124

10
[ 100945-15-1 ]
[ 89524-99-2 ]

Reference： [1] Tetrahedron Letters, 1989, vol. 30, # 38, p. 5121 - 5124

[ 89524-99-2 ] Synthesis Path-Downstream 1~10

1
[ 57476-50-3 ]
[ 89524-99-2 ]
[ 89525-16-6 ]
[ 89525-16-6 ]

Reference： [1]Synthesis,1984,p. 53 - 60

2
[ 89524-99-2 ]
[ 2120-70-9 ]
[ 141540-70-7 ]
[ 141540-70-7 ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 2373 - 2384

3
[ 638-54-0 ]
[ 89524-99-2 ]
(2Z,10Z)-2,11-Bis-acetylamino-dodeca-2,10-dienedioic acid dimethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane 1.) 5-10 deg C, 1 h, 2.) room temp., overnight;

Reference： [1]Hiebl, Johann; Kollmann, Hermann; Rovenszky, Franz; Winkler, Karin [Journal of Organic Chemistry, 1999, vol. 64, # 6, p. 1947 - 1952]

4
[ 932-41-2 ]
[ 89524-99-2 ]
[ 253332-82-0 ]
[ 253332-81-9 ]

Yield	Reaction Conditions	Operation in experiment
38%; 41%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20℃; for 1h;	2,3-Thiophene dicarboxaldehyde (1.40 G, 9.99 mmol) is dissolved in CHZCLZ (100 mL) and the flask is placed in an ice bath. C153 (2.63 g, 11.0 mmol) is dissolved in CH2C12 (50 mL), DBU (1.65 mL, 11.0 mmol) is added, and this solution is added drop-wise to the chilled thiophene solution. The reaction mixture is stirred for 1 h while the flask is in an ice bath and then over night at rt. The reaction is concentrated in vacuo and the crude material is chromatographed over 300 g slurry-packed silica eluting with 50% ETOAC/HEXANE. The fractions are collected in two different groups to obtain the desired compounds. Each group of fractions is combined and concentrated separately. Methyl thieno [2,3-c] pyridine-5-carboxylate (C154) elutes first and the appropriate fractions are concentrated to give a white solid (41% yield). The second group of appropriate fractions are collected and concentrated to give methyl thieno [3,2-c] PYRIDINE-6-CARBOXYLATE (C155) as a yellow solid (38% yield). MS (EI) for C154 for C9H7NO2S, M/Z : 193 (M) +. MS (EI) for C155 for C9H7N02S, M/Z : 193 (M) +.

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 7935 - 7938
[2]Patent: WO2004/39815,2004,A2 .Location in patent: Page 53

5
[ 4122-56-9 ]
[ 89524-99-2 ]
[ 69454-42-8 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 7935 - 7938

6
[ 7149-49-7 ]
[ 89524-99-2 ]
benzo[<i>g</i>]isoquinoline-3-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 7935 - 7938

7
[ 89524-99-2 ]
[ 643-79-8 ]
[ 27104-73-0 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 7935 - 7938

8
[ 932-41-2 ]
[ 89524-99-2 ]
[ 253332-82-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;	2,3-Thiophene dicarboxaldehyde (1.40 g, 9.99 mmol) is dissolved in CH2Cl2 (100 mL) and the flask is placed in an ice bath. C153 (2.63 g, 11.0 mmol) is dissolved in CH2Cl2 (50 mL), DBU (1.65 mL, 11.0 mmol) is added, and this solution is added drop-wise to the chilled thiophene solution. The reaction mixture is stirred for 1 h while the flask is in an ice bath and then over night at rt. The reaction is concentrated in vacuo, and the crude material is chromatographed over 300 g slurry-packed silica eluding with 50% EtOAc/hexane. The fractions are collected in two different groups to obtain the desired compounds. Each group of fractions is combined and concentrated separately. Methyl thieno[2,3-c]pyridine-5-carboxylate (C154) elutes first and the appropriate fractions are concentrated to give a white solid (41% yield). The second group of appropriate fractions are collected and concentrated to give methyl thieno[3,2-c]pyridine-6-carboxylate (C155) as a yellow solid (38% yield). MS (EI) for C154 for C9H7NO2S, m/z: 193 (M)+. MS (EI) for C155 for C9H7NO2S, m/z: 193 (M)+.

Reference： [1]Patent: US2003/45540,2003,A1

9
[ 932-41-2 ]
[ 89524-99-2 ]
[ 253332-81-9 ]

Yield	Reaction Conditions	Operation in experiment
54%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0℃; for 1.5h;	To a mixture of thiophene-2,3-dicarbaldehyde (2.0 g, 14 mmol) and methyl 2-acetamido- 2-(dimethoxyph osphoryl)acetate (3.4 g, 14 mmol) in dichloromethane (20 mL) at 0 C was added dropwisel,8-diazabicyclo[5.4.0]undec-7-ene (2.4 g, 16 mmol). The mixture was stirred at 0 C for 1.5 hours. On completion, the reaction mixture was quenched with water and extracted with dichloromethane (3 x 50 mL). The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography [petroleum ether: ethyl acetate = 10: 1] to give compound B-147 (1.5 g, 54% yield) as a white solid.
54%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0℃; for 1h;Cooling with ice;	(A) A solution of 997 methyl 2-acetamido-2-(dimethoxyphosphoryl)acetate (8.45 g, 35.3 mmol) and 974 DBU (5.38 g, 35.3 mmol) in 10 DCM (50 mL) was added in drop-wise fashion to an ice-cooled solution of 998 <strong>[932-41-2]2,3-thiophene dicarboxaldehyde</strong> (4.5 g, 32.1 mmol) in DCM (150 mL). After stirring at 0 C. for 1 h, the mixture was allowed to stir at rt overnight. The reaction was then concentrated under reduced pressure and the resultant residue was purified by silica gel chromatography (0-50% EtOAc/petroleum ether) to afford of 999 methyl thieno[2,3-c]pyridine-5-carboxylate (3.3 g, 54%), as a white solid. LC/MS: mass calcd. for C9H7NO2S: 193.02, found: 193.9 [M+H]+

Reference： [1]Patent: WO2016/100184,2016,A1 .Location in patent: Paragraph 00357-00358
[2]Patent: US2017/291908,2017,A1 .Location in patent: Paragraph 0771

10
[ 67-36-7 ]
[ 89524-99-2 ]
C₁₈H₁₇NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94.6%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 5 - 15℃; for 2h;	1 Example 1: Synthesis of compound 6 To a round-bottom flask were added compound 1 (134.0 g), compound 2 (212.3 g) and DCM (675 mL). DBE1 (133.8 g) was added dropwise at 5~15°C. After 2 h, the reaction mixture was quenched with EbO. Acetic acid was added to adjust pH=6~7. The layers were separated. The aqueous phase was extracted with DCM twice. The organic phases were combined and concentrated. The mixture was added MTBE and stirred at room temperature for 1 h. The suspension was filtered to give compound 3 as an off-white solid (199.2 g, 94.6% yield, 96.0% purity). NMR (400 MHz, CDCh) d 7.47 - 7.35 (m, 2H), 7.40 - 7.34 (m, 4H), 7.22 - 7.13 (m, 1H), 7.06 - 7.02 (m, 2H), 6.98 - 6.92 (m, 2H), 3.82 (s, 3H), 2.12 (s, 3H).Mass: [M+H]+: 312.3;
94.6%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 5 - 15℃; for 2h;	2 Synthesis of methyl 2-acetamido-3-(4-phenoxyphenyl) propionate (6) 134.0 g of compound 3 and 212.3 g of compound 4 were added to the reaction flask, 675 mL of DCM was added, stirring was started, 133.8 g of DBU was added dropwise under temperature control at 5 to 15 °C, the reaction was performed for 2 h, and HPLC monitored the complete conversion of raw materials, and 804 mL of water was added. The reaction was quenched, acetic acid was added dropwise to adjust the pH to 6-7, and after stirring for 10 min, the solution was separated, and the aqueous phase was extracted with 402 mL of DCM, which was repeated twice. The combined organic phases were concentrated to 1 vol under reduced pressure at 35°C, a white solid was precipitated, 536 mL of MTBE was added to make a slurry for 1 h, suction filtered, and the filter cake was rinsed with 134 mL of MTBE to obtain 199.2 g of off-white solid compound 5, yield 94.6%, purity 96.0%.

Reference： [1]Current Patent Assignee: SUZHOU PENGXU PHARMATECH CO., LTD.; NANJING F S PHARMATECH - WO2021/252295, 2021, A1 Location in patent: Paragraph 0036
[2]Current Patent Assignee: SUZHOU PENGXU PHARMATECH CO LTD - CN114436878, 2022, A Location in patent: Paragraph 0023-0025

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H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
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

[ CAS No. 89524-99-2 ] {[proInfo.proName]}

Quality Control of [ 89524-99-2 ]

Related Doc. of [ 89524-99-2 ]

Product Details of [ 89524-99-2 ]

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Application In Synthesis of [ 89524-99-2 ]

[ 89524-99-2 ] Synthesis Path-Upstream 1~10

[ 89524-99-2 ] Synthesis Path-Downstream 1~10

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