Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 124931-12-0 | MDL No. : | MFCD00134233 |
Formula : | C8H18NO5P | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 239.21 g/mol | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
![]() |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With sodium hydride In diethyl ether for 1h; 0 deg C to room temperature; | |
50% | With sodium hydride In tetrahydrofuran at -78 - 20℃; for 17h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With n-butyllithium In tetrahydrofuran; hexane for 24h; Ambient temperature; | |
With sodium hydride In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | ||
1.43 g | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In 1,4-dioxane at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2,6,6-trimethylcyclohex-1-enecarbaldehyde In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 73% 2: 4.6% | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: (2R)-1-(tert-butyloxycarbonyl)-2-((tert-butyldiphenylsilyl)oxymethyl)-3-azetidinone In tetrahydrofuran at 20℃; for 14h; | |
1: 67% 2: 7.7% | In methanol at -78 - 20℃; for 25h; | |
With sodium hydride In tetrahydrofuran at 0℃; Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium hydride In diethyl ether for 1h; 0 deg C to room temperature; | |
With n-butyllithium 1.) THF, -78 deg C, 2.) 0 deg C, 1 h; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: benzaldehyde In tetrahydrofuran at -78 - 20℃; | HWE Reaction; General Procedure A General procedure: Diethyl 2-[methoxy(methyl)amino]-2-oxoethylphosphonate (1; 1.2 equiv) was dissolved in anhyd THF and NaH (1.2 equiv) was added portionwise at r.t. until gas evolution ceased. The mixture was then cooled to -78 °C and the appropriate benzaldehyde derivative (1 equiv) dissolved in anhyd THF was added. The reaction mixture was stirred at -78 °C for 1 h, then allowed to warm to r.t. and stirred overnight. H2O (10 mL) was added, the layers were separated, and the organic layer was washed with sat. aq NaHCO3 (2 × 10 mL). The combined aqueous phases were extracted with EtOAc (3 × 15 mL). The combined organic phases were then washed with brine (2 × 10 mL) ,dried (MgSO4), and concentrated in vacuo. If necessary, the crude product was purified by flash column chromatography (FCC) using the indicated eluent. |
91% | With sodium hydride In diethyl ether for 1h; 0 deg C to room temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | at 100℃; for 18h; | A solution of <strong>[67442-07-3]2-chloro-N-methoxy-N-methylacetamide</strong> (2.48 g,17.7 mmol) and triethyl phosphite (3.00 mL, 17.7 mmol) was heated to 100 °C for 18 h. The crude product was purified by flash column chromatography (0?2percent MeOH in CH2Cl2) to give 1 as a colorless oil; yield: 3.31 g (13.8 mmol; 78percent); Rf = 0.42 (2percent MeOH in CH2Cl2); HPLC purity (method b): >95percent (210 nm), >95percent (254 nm). IR (ATR): 2985, 2940, 2908, 1659, 1381, 1253, 1050, 1020, 998, 961 cm?1. 1H NMR (400 MHz, CDCl3): delta = 4.26?4.07 (m, 4 H, 2 × OCH2CH3), 3.76(s, 3 H, OCH3), 3.20 (s, 3 H, NCH3), 3.15 (d, J = 22.1 Hz, 2 H, 1-H), 1.33(td, J = 7.1, 0.6 Hz, 6 H, 2 × OCH2CH3). 13C NMR (101 MHz, CDCl3): delta = 166.2 (C-2), 62.7 (2 × OCH2CH3), 61.6(OCH3), 32.3 (NCH3), 30.9 (C-1), 16.5 (2 × OCH2CH3). HRMS (ESI): m/z [M + H]+ calcd for C8H19NO5P+: 240.0995; found: 240.0996. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium <i>tert</i>-butylate | |
80% | With potassium <i>tert</i>-butylate In tetrahydrofuran 1.) 0 deg C, 30 min, 2.) -78 deg C, 1 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With n-butyllithium In tetrahydrofuran at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With sodium methylate In tetrahydrofuran at 20℃; for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran at -78 - 20℃; | HWE Reaction; General Procedure A General procedure: Diethyl 2-[methoxy(methyl)amino]-2-oxoethylphosphonate (1; 1.2 equiv) was dissolved in anhyd THF and NaH (1.2 equiv) was added portionwise at r.t. until gas evolution ceased. The mixture was then cooled to -78 °C and the appropriate benzaldehyde derivative (1 equiv) dissolved in anhyd THF was added. The reaction mixture was stirred at -78 °C for 1 h, then allowed to warm to r.t. and stirred overnight. H2O (10 mL) was added, the layers were separated, and the organic layer was washed with sat. aq NaHCO3 (2 × 10 mL). The combined aqueous phases were extracted with EtOAc (3 × 15 mL). The combined organic phases were then washed with brine (2 × 10 mL) ,dried (MgSO4), and concentrated in vacuo. If necessary, the crude product was purified by flash column chromatography (FCC) using the indicated eluent. |
97% | With sodium methylate In tetrahydrofuran at 20℃; for 0.333333h; | |
93% | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at -10 - 0℃; Inert atmosphere; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran at -10 - 20℃; Inert atmosphere; |
66% | With sodium hydride In tetrahydrofuran at -78 - 20℃; for 17h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: (2R)-2-benzyloxycarbonylamino-3-(4-methoxybenzylsulfanyl)-succinic acid 1-methyl ester 4-tert-butyl ester With diisobutylaluminium hydride In tetrahydrofuran; hexane; toluene at -78 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With methyllithium In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 3,6-diphenyl-3,6-dihydro-1,2-dioxine In tetrahydrofuran for 3h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With methyllithium In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 3-phenyl-3,6-dihydro-1,2-dioxine In tetrahydrofuran for 3h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sodium hydride In tetrahydrofuran at 20℃; | |
92% | With sodium hydride In tetrahydrofuran at 20℃; for 1.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 57% 2: 35% | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: (2S,4RS)-5-(tert-butyldimethylsilyloxy)-2-methyl-4-(trimethoxymethylphenyl)pentanal In tetrahydrofuran at 20℃; for 2.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With sodium hydride In tetrahydrofuran at 0 - 20℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.171 g | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: C28H44O10 In tetrahydrofuran at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1.16667h; Stage #2: (5Z,7E)-(3R,4R)-4-(tert-butyldimethylsilanyloxy)-10-(tert-butyldiphenylsilanyloxy)-3-methyldeca-5,7-dienal In tetrahydrofuran at 20℃; for 1.16667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In acetonitrile at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: [6-fluoro-1-(4-toluenesulfonyl)indol-3-yl]carboxaldehyde In tetrahydrofuran at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: [4-fluoro-1-(4-toluenesulfonyl)indol-3-yl]carboxaldehyde In tetrahydrofuran at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: [7-fluoro-1-(4-toluenesulfonyl)indol-3-yl]carboxaldehyde In tetrahydrofuran at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 3-formyl-1-(4-toluenesulfonyl)-1H-indole-6-carbonitrile In tetrahydrofuran at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 3-formyl-1-(4-toluenesulfonyl)-1H-indole-4-carbonitrile In tetrahydrofuran at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: 3-formyl-1-(toluene-4-sulfonyl)-1H-indole-5-carbonitrile In tetrahydrofuran at 0℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 3-formyl-1-(4-toluenesulfonyl)-1H-indole-7-carbonitrile In tetrahydrofuran at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 5-fluoro-1-(p-tolylsulfonyl)indole-3-carboxaldehyde In tetrahydrofuran at 0℃; | |
88% | In tetrahydrofuran | 2 Trans-1-(N,N-dimethylaminomethyl)-2-[5-fluoroindol-3-yl]cyclopropane A solution of diethyl (N-methoxy-N-methylcarbamoylmethyl) phosphonate (5.64 ml, 6.54 g, 27.4 mmol) in anhydrous tetrahydrofuran (25 ml) was added to a stirred suspension of oil free sodium hydride (1.05 g, 27.4 mmol) in anhydrous tetrahydrofuran (350 ml) maintained at 0° C. The reaction was warmed to room temperature and was stirred for 2 h. After cooling to 0° C., [5-fluoro-1-(p-toluenesulfonyl)indol-3-yl]carboxaldehyde (7.24 g, 22.8 mmol) was added. The resulting mixture was stirred at 0° C. for 30 min. The reaction was quenched with aqueous hydrochloric acid (0.1 N) and poured into water (150 ml). After being made acidic with hydrochloric acid (1.0 N), the aqueous portion was extracted with ethyl acetate (3*100 ml). The combined organic layers were washed with brine (50 ml) and dried over anhydrous sodium sulfate. The filtrate was concentrated in vacuo. The crude product was purified by recrystallization from ethyl acetate to afford a total of 8.03 g (88% yield) of (E)-[5-fluoro-1-(p-toluenesulfonyl)indol-3-yl]-N-methoxy-N-methylacrylamide as a white solid: mp 199-200° C. (dec.); 1H NMR (400 MHz, DMSO-d6) 8.56 (1 H, s), 7.99 (1 H, m), 7.93 (2 H, d, J=8.4 Hz), 7.68 (2 H, m), 7.42 (2 H, d, J=8.1 Hz), 7.28 (1 H, t, J=9.2 Hz), 7.12 (1 H, d, J=16 Hz), 3.77 (3 H, s), 3.22 (3 H, s), 2.33 (3 H, s); MS m/e 403 (M+H)+. Anal. Calcd. For C20H19FN2O4S: C, 59.69; H, 4.75; N 6.96. Found: C, 59.60; H, 4.70; N, 6.86. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: Cyclopropanecarboxaldehyde In tetrahydrofuran at 20℃; for 2h; Further stages.; | |
79% | Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: Cyclopropanecarboxaldehyde In tetrahydrofuran at 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With NaH In tetrahydrofuran | 63.3 (2-{2,3-Difluoro-4-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]phenyl}cyclopropyl)acetic acid Trifluoroacetate. Step 3: (2E)-3-(2,3-Difluoro-4-methoxyphenyl)-N-methoxy-N-methylprop-2-enamide. Diethyl (N-methoxy-N-methylcarbamoylmethyl)-phosphonate (4.8 g) was added to a suspension of 95% NaH (550 mg) in THF (40 mL) under nitrogen atmosphere. The mixture was stirred at an ambient temperature for 10 minutes, and was treated with the product of step 2 (3.44 grams). The mixture was stirred at room temperature for 1 hour and was quenched with water (10 mL). The mixture was concentrated in vacuoo afforded an oily residue. The residue was extracted with ethyl acetate, washed with water, dried (Na2SO4) and concentrated to yield 3.2 grams of the title compound as white solid. 1H-NMR(CDCl3): 7.72 (d, 1H), 7.22(m, 1H), 7.15(d, 1H), 6.75(m,1H), 3.92(s, 3H), 3.78(s, 3H), 3.3(s, 3H). |