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[ CAS No. 114676-69-6 ]

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Chemical Structure| 114676-69-6
Chemical Structure| 114676-69-6
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CAS No. :114676-69-6 MDL No. :MFCD00797548
Formula : C11H19NO5 Boiling Point : 335.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :245.27 g/mol Pubchem ID :6951202
Synonyms :

Safety of [ 114676-69-6 ]

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:

Application In Synthesis of [ 114676-69-6 ]

  • Upstream synthesis route of [ 114676-69-6 ]
  • Downstream synthetic route of [ 114676-69-6 ]

[ 114676-69-6 ] Synthesis Path-Upstream   1~6

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  • [ 135042-12-5 ]
Reference: [1] Patent: US2014/315883, 2014, A1, . Location in patent: Paragraph 0319; 0320
[2] Patent: WO2014/169473, 2014, A1, . Location in patent: Page/Page column 66
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Reference: [1] Journal of Medicinal Chemistry, 1988, vol. 31, # 8, p. 1598 - 1611
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  • [ 114676-61-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1988, vol. 31, # 8, p. 1598 - 1611
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  • [ 254881-77-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 26, p. 4948 - 4963
[2] Patent: WO2016/34134, 2016, A1,
[3] Journal of Organic Chemistry, 2018, vol. 83, # 8, p. 4491 - 4504
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  • [ 256487-77-1 ]
YieldReaction ConditionsOperation in experiment
84% With dipyridinium dichromate In dichloromethane at 20℃; Preparation 6 4-chloro-6-fluoropyrrolo[l,2-b]pyridazine-3-carboxamideStep 1 : (R)- 1 -tert-butyl 2-methyl 4-oxopyrrolidine-l,2-dicarboxylate[00179] To slurry of pyridinium dichromate (9.97 g, 26.5 mmol) indichloromethane (60 mL) at rt was added (2R,4R)-1 -tert-butyl 2-methyl 4- hydroxypyrrolidine-l,2-dicarboxylate (5.00 g, 20.39 mmol) in several portions. The resulting mixture was stirred overnight at rt. Celite (5g) was added and the mixture stirred for 40 min, filtered and the filter cake was rinsed with additionaldichloromethane (50 mL x 3). The resulting filtrate was concentrated and toluene (40 mL) was added followed by concentration again under vacuum to give ~ 6.5 g of a brown syrup as the crude product. Purification by flash silica gel chromatography (120g column, EtOAc in hexane, 0 to 100percent gradiant, 85 mL/min) afforded 4.18 g (84percent>) of the title compound as a white solid. LCMS (condition A): m/z 144 (M-Boc) -ve. XH NMR (400 MHz, CDCl3) δ ppm 4.64-4.89 (1 H, m), 3.84-3.96 (2 H, m), 3.77 (3 H, s), 2.81-3.10 (1 H, m), 2.59 (1 H, dd, J=18.93, 1.76 Hz), 1.52 (9 H, s).
84% With dipyridinium dichromate In dichloromethane at 20℃; To slurry of pyridinium dichromate (9.97 g, 26.5 mmol) indichloromethane (60 mL) at rt was added (2R,4R)- 1 -tert-butyl 2-methyl 4- hydroxypyrrolidine-l,2-dicarboxylate (5.00 g, 20.39 mmol) in several portions. The resulting mixture was stirred overnight at rt. Celite (5g) was added and the mixture stirred for 40 min, filtered and the filter cake was rinsed with additionaldichloromethane (50 mL x 3). The resulting filtrate was concentrated and toluene (40 mL) was added followed by concentration again under vacuum to give ~ 6.5 g of a brown syrup as the crude product. Purification by flash silica gel chromatography (120g column, EtOAc in Hexane, 0 to 100percent gradiant, 85 mL/min) afforded 4.18 g (84percent>) of the title compound as a white solid. LCMS (condition A): m/z 144 (M-Boc) -ve. XH NMR (400 MHz, CDCl3) δ ppm 4.64-4.89 (1 H, m), 3.84-3.96 (2 H, m), 3.77 (3 H, s), 2.81-3.10 (1 H, m), 2.59 (1 H, dd, J=18.93, 1.76 Hz), 1.52 (9 H, s).
72% With Dess-Martin periodane In dichloromethane at 20℃; for 2 h; Scheme 4. Step A: Stir a mixture of N-te^butyl-cz's-4-hydroxy-D-proline methyl ester (2.0 g, 7.91 mmol), the Dess-Martin periodinane (4.84 g, 11.07 mmol), and CH2CI2 (10 mL) at room temperature for 2 h. Add CH2CI2 (150 mL), saturated aqueous NaHC03 (75 mL), and water (75 mL), then separate the layers and extract the aqueous layer with CH2CI2 (100 mL). Combine the organic phases, dry over MgS04, filter, and concentrate the filtrate under reduced pressure. Subject the resulting crude material to flash chromatography on silica gel, eluting with a gradient of 0percent to 50percent EtOAc in hexanes, to furnish the title compound (1.39 g, 72percent yield). Mass spectrum (m/z): 144 (M + 2H - Boc)+, 188 (M + 2H - t-Bu)+.
59.8% With Dess-Martin periodane In dichloromethane at 20℃; for 4 h; At room temperature,3C (14.92 g, 60.87 mmol) was dissolved in dichloromethane (100 mL)Add to Martin in batches(51.63 mg, 121.73 mmol),The reaction was stirred at room temperature for 4 hours.After cooling to 0 ° C, the sodium bicarbonate solution was added dropwise to the reaction solution until no more bubbles were generated, and a white solid was precipitated.The reaction solution was filtered and the filter cake was washed with methyl tertiary butyl ether (50 mL x 3) and the filtrate was extracted with methyl tertiary butyl ether (30 mL x 2).The organic phase was washed with saturated sodium chloride solution (50 mL x 2), dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure to give pale yellow liquid 3D (10.3 g, yield 59.8percent).
48%
Stage #1: With sodium hydrogencarbonate; Dess-Martin periodane In dichloromethane at 23℃; for 4 h;
Stage #2: With sodium hyposulfite In dichloromethane; water
Preparation of [1- (3, 4-DIMETHOXY-5-TRIFLUOROMETHYLTHIOBENZOYL)-4-ETHYNYL-2, 5-DIHYDRO-LH-] [PYRROLE-2R-CARBOXYLIC] acid hydroxyamide [100570]] Step 1: To a stirred solution of 4R-hydroxypyrrolidine-1,2R-dicarboxylic acid 1- [TERT-BUTYL] ester 2-methyl ester [(30.] 4 g, 0.124 mol, 1.0 eq.; product from Step 2 of Example 90) in [CH2C12] [(800] mL) at [23°C,] was added NaHCO3 (103 g, 1.23 mol, 10.0 eq. ), followed by Dess- Martin periodinane (61 g, 0.144 mol, 1. 16 eq. ). After being stirred at [23 °C] for 1 h, another batch of Dess-Martin periodinane (14 g, 0.033 mol, 0.27 eq. ) was added. After 3 h, the reaction mixture was quenched by addition of aqueous solution [OF NA2S203] and extracted with [CH2CL2] (3 x 300 mL). The combined organic layer was washed with brine, dried [(NA2S04)] and concentrated in [VACUUM.] The residue was chromatographed on silica gel (EtOAc/Hexane : [0percent-40percent)] to afford 4-oxopyrrolidine-1, 2R-dicarboxylic acid [1-TERT-BUTYL] ester 2-methyl ester (14.3 g, 48percent).

Reference: [1] Patent: WO2012/125887, 2012, A1, . Location in patent: Page/Page column 74-75
[2] Patent: WO2012/125886, 2012, A1, . Location in patent: Page/Page column 85
[3] Patent: WO2015/94902, 2015, A1, . Location in patent: Page/Page column 20; 21
[4] Journal of Medicinal Chemistry, 1999, vol. 42, # 26, p. 5426 - 5436
[5] Patent: TW2017/8221, 2017, A, . Location in patent: Page/Page column 41; 42
[6] Patent: WO2004/7444, 2004, A2, . Location in patent: Page 142
[7] Patent: WO2004/87646, 2004, A2, . Location in patent: Page/Page column 71
[8] Patent: WO2011/130383, 2011, A1, . Location in patent: Page/Page column 87-88
[9] Patent: WO2012/54510, 2012, A1, . Location in patent: Page/Page column 95
[10] Patent: WO2012/162635, 2012, A1, . Location in patent: Page/Page column 149-150
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Reference: [1] Patent: WO2011/130383, 2011, A1,
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