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[ CAS No. 69651-48-5 ] {[proInfo.proName]}

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Chemical Structure| 69651-48-5
Chemical Structure| 69651-48-5
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Product Details of [ 69651-48-5 ]

CAS No. :69651-48-5 MDL No. :MFCD01860630
Formula : C13H17NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :LRWJRIFKJPPAPM-JTQLQIEISA-N
M.W : 267.28 Pubchem ID :11300124
Synonyms :
Chemical Name :(S)-2-((tert-Butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetic acid

Calculated chemistry of [ 69651-48-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.38
Num. rotatable bonds : 6
Num. H-bond acceptors : 5.0
Num. H-bond donors : 3.0
Molar Refractivity : 68.56
TPSA : 95.86 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.99
Log Po/w (XLOGP3) : 1.86
Log Po/w (WLOGP) : 1.72
Log Po/w (MLOGP) : 1.16
Log Po/w (SILICOS-IT) : 0.78
Consensus Log Po/w : 1.5

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.51
Solubility : 0.832 mg/ml ; 0.00311 mol/l
Class : Soluble
Log S (Ali) : -3.49
Solubility : 0.0856 mg/ml ; 0.00032 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.2
Solubility : 1.7 mg/ml ; 0.00635 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.55

Safety of [ 69651-48-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 69651-48-5 ]

* 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 [ 69651-48-5 ]
  • Downstream synthetic route of [ 69651-48-5 ]

[ 69651-48-5 ] Synthesis Path-Upstream   1~4

  • 1
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  • [ 32462-30-9 ]
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YieldReaction ConditionsOperation in experiment
100% With sodium hydrogencarbonate In 1,4-dioxane; water at 0 - 20℃; for 18 h; To a solution of L-4-hydroxyphenylglycine (1.00 g, 5.98 mmol) and sodium hydrogencarbonate (2.50 g, 29.11 mmol) in a mixture of 1,4-dioxane (20 mL) and water (20 mL) was added di-tert-butyl dicarbonate (1.40 g, 6.58 mmol) at 0 0C, followed by stirring at room temperature for 18 hours. The organic portion of the solvent was evaporated, and the reaction mixture was partitioned between ethyl acetate (300 mL) and 0.5M aqueous hydrochloric acid (50 mL). The organic layer was separated and washed with 0.5M aqueous hydrochloric acid, water and brine, dried over sodium sulfate, filtered and the solvent concentrated to give (S)-2-(tert- butoxycarbonylamino)-2-(4-hydroxyphenyl)acetic acid (1.6 g, quantitative). 1H NMR (400 MHz, CDCl3): 8.80 (bs, IH), 7.12 (d, 2H), 6.62 (d, 2H), 5.80 (d, IH), 5.00 (d, IH), 1.22 (s, 9H). MS (EI) for CnHi7NO5: 266 (M-H). [00989]
99% at 20℃; 4-Hydroxy-L-phenylglycine (4.00 g, 23.93 mmol) and sodium bicarbonate (6.04 g, 71.80 mmol) was dissolved in water/tetrahydrofuran (70 mL/70 mL). The solution was cooled in an ice-bath and then di-tert-butyl dicarbonate (7.83 g, 35.90 mmol) was added into the solution. After stirring at room temperature overnight the mixture was washed with ether (50 mL). The aqueous portion was acidified to pH 4 with 2N HC1 and extracted with dichloromethane (3 x 100 mL). The organic portion was washed with saturated sodium chloride (60 mL) and dried over anhydrous sodium sulfate. The organic portion was filtered, concentrated, and dried under high vacuum to give 6.35 g product as a white solid (yield: 99percent). NMR (500 MHz, CD3OD): δ 7.22 (d, 2H), 6.77 (d, 2H), 5.07 (br, 1 H), 1.45 (s, 9H); MS (EI) for C,3Hi7N05: 266 (MH").
86% With triethylamine In tetrahydrofuran; water at 0℃; for 18 h; To a solution of (S)-2-amino-2-(4-hydroxyphenyl)acetic acid (2.00 g, 11.96 mmol) and Et3N (1.67 mL, 11.96 mmol) in THF (30 mL) and H2O (30 mL) at 0° C. was added di-tert-butyl dicarbonate (2.61 g. 11.96 mmol).
The solution was stirred at 0° C. for 18 hours and then concentrated in vacuo.
The residue was diluted with ethyl acetate and washed with 5percent H3PO4 aqueous solution.
The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound as a light colored solid.
The crude material was taken on directly to the next step. (2.85 g, 86percent yield) MS (ESI+) m/z=290 (M+Na)+
Reference: [1] Synlett, 2008, # 15, p. 2355 - 2359
[2] Patent: WO2009/55077, 2009, A1, . Location in patent: Page/Page column 410
[3] Chemistry - A European Journal, 2010, vol. 16, # 34, p. 10523 - 10534
[4] Patent: WO2014/210436, 2014, A2, . Location in patent: Paragraph 00411; 00412
[5] Advanced Synthesis and Catalysis, 2017, vol. 359, # 17, p. 2897 - 2900
[6] Patent: WO2018/149419, 2018, A1, . Location in patent: Paragraph 00539
[7] Patent: US2010/29686, 2010, A1, . Location in patent: Page/Page column 73
[8] Journal of Organic Chemistry, 2013, vol. 78, # 13, p. 6412 - 6426
[9] Heterocycles, 1994, vol. 39, # 2, p. 603 - 612
[10] Tetrahedron Letters, 2007, vol. 48, # 26, p. 4509 - 4513
[11] Journal of the American Chemical Society, 2007, vol. 129, # 51, p. 15830 - 15838
[12] Patent: WO2009/34388, 2009, A1, . Location in patent: Page/Page column 23
[13] Journal of the American Chemical Society, 2011, vol. 133, # 44, p. 17869 - 17877
[14] Patent: US9187524, 2015, B2, . Location in patent: Page/Page column 98; 99
[15] Patent: WO2017/84629, 2017, A1, . Location in patent: Paragraph 00254
[16] Patent: WO2017/84630, 2017, A1, . Location in patent: Paragraph 00377
[17] Patent: WO2008/134679, 2008, A1, . Location in patent: Page/Page column 98
  • 2
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YieldReaction ConditionsOperation in experiment
89%
Stage #1: With sodium bromide In acetonitrile for 2 h; Reflux
Stage #2: at 65℃; for 20 h; Reflux
General procedure: (I) In a reaction vessel equipped with a stirrer, a condensing reflux device and a thermometer, a mass fraction of 65percentC eye solution200 ml,D- (a) -p-hydroxyphenylglycine 0.085mol, sodium bromide 0.08mol, stirring speed 190rpm, stirring time 120min, tert-butoxycarbonyl bromide 0.085mol, control solution temperature 65 , reaction time 20h, adding 500ml mass fraction 40 percent potassium bromide solution was diluted, ethylenediamine was extracted 8 times, the aqueous layer was washed with oxalic acid, and the pH value of the control solution was 6. After adding potassium bromide, the mass fraction was 96percent. The extract was extracted with calcium chloride, , 1.9kPa vacuum distillation, evaporation of the solvent, the residue added to the mass fraction of 95percent butanol solution, the solid crushing, filtration, D-α-tert-butoxycarbonylamino-α- (4-hydroxyphenyl) - acetic acid 14.62 g, yield 89percent.
Reference: [1] Patent: CN105585510, 2016, A, . Location in patent: Paragraph 0014; 0015; 0006
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Reference: [1] Patent: US6353099, 2002, B1, . Location in patent: Page column 29
  • 4
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  • [ 22818-40-2 ]
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Reference: [1] Tetrahedron, 1983, vol. 39, # 15, p. 2563 - 2570
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