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[ CAS No. 23680-31-1 ] {[proInfo.proName]}

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Chemical Structure| 23680-31-1
Chemical Structure| 23680-31-1
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Product Details of [ 23680-31-1 ]

CAS No. :23680-31-1 MDL No. :MFCD00066063
Formula : C15H21NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :295.33 Pubchem ID :-
Synonyms :
(S)-3-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

Calculated chemistry of [ 23680-31-1 ]

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.47
Num. rotatable bonds : 9
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 77.23
TPSA : 84.86 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) : -6.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.58
Log Po/w (XLOGP3) : 1.9
Log Po/w (WLOGP) : 2.03
Log Po/w (MLOGP) : 1.41
Log Po/w (SILICOS-IT) : 1.6
Consensus Log Po/w : 1.9

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.49
Solubility : 0.966 mg/ml ; 0.00327 mol/l
Class : Soluble
Log S (Ali) : -3.3
Solubility : 0.146 mg/ml ; 0.000496 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.31
Solubility : 0.144 mg/ml ; 0.000488 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.21

Safety of [ 23680-31-1 ]

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 [ 23680-31-1 ]

* 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 [ 23680-31-1 ]
  • Downstream synthetic route of [ 23680-31-1 ]

[ 23680-31-1 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 23680-31-1 ]
  • [ 108-95-2 ]
  • [ 17176-77-1 ]
Reference: [1] Patent: US2004/121316, 2004, A1,
[2] Patent: US2005/239054, 2005, A1,
  • 2
  • [ 23680-31-1 ]
  • [ 67321-05-5 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 8, p. 1272 - 1280
  • 3
  • [ 23680-31-1 ]
  • [ 4726-96-9 ]
YieldReaction ConditionsOperation in experiment
62.3% With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 2 h; The compound obtained in the previous step was dissolved in an appropriate amount of dry distilled DCM,TFA 1.0mL, triethylsilane 0.1mL, the reaction was stirred at room temperature for 2h,The reaction was complete by TLC.The solvent was distilled off under reduced pressure,Add saturated sodium bicarbonate solution to adjust the pH to 7 ~ 8,Then add DCM,Wash twice with saturated saline, concentrate the organic phase to give a yellow oily liquid.Silica gel column chromatography (chloroform: methanol = 15: 1) gave a yellow powdery solid in a yield of 62.3percent.
Reference: [1] Patent: CN107082754, 2017, A, . Location in patent: Paragraph 0119; 0124
[2] Organic Process Research and Development, 2003, vol. 7, # 4, p. 521 - 532
[3] Tetrahedron Letters, 2014, vol. 55, # 30, p. 4149 - 4151
[4] ACS Chemical Neuroscience, 2017, vol. 8, # 8, p. 1681 - 1687
[5] Patent: WO2017/189866, 2017, A1, . Location in patent: Paragraph 0210
  • 4
  • [ 23680-31-1 ]
  • [ 58577-87-0 ]
Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 35, p. 6445 - 6448
  • 5
  • [ 23680-31-1 ]
  • [ 501-53-1 ]
  • [ 20806-43-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1979, vol. 22, p. 935 - 943
  • 6
  • [ 3262-72-4 ]
  • [ 100-39-0 ]
  • [ 23680-31-1 ]
YieldReaction ConditionsOperation in experiment
80% With NaH In water; ethyl acetate; N,N-dimethyl-formamide; mineral oil Example 36
N-tert-Butoxycarbonyl-O-benzyl-L-serine 39:
To a solution of Boc-L-serine (15 g, 73.09 mmol) in DMF (300 mL) at 0° C. was added NaH (6.43 g, 160.80 mmol, 60percent in mineral oil) and stirred for 1.5 h at 0° C.
After the addition of benzyl bromide (13.75 g, 80.40 mmol), the reaction mixture was warmed to room temperature and stirred overnight.
The solvent was evaporated under reduced pressure and the residue was dissolved in H2O.
The crude product was partitioned between H2O and Et2O.
The aqueous phase was acidified to pH<4 with 3 N HCl and extracted with EtOAc three times.
The combined EtOAc solution was washed with H2O, dried with Na2SO4, filtered, and concentrated to give the N-tert-butoxycarbonyl-O-benzyl-L-serine (17.27 g, 80percent).
80% With NaH In water; ethyl acetate; N,N-dimethyl-formamide; mineral oil Example H36
N-tert-Butoxycarbonyl-O-benzyl-L-serine 39:
To a solution of Boc-L-serine (15 g, 73.09 mmol) in DMF (300 mL) at 0° C. was added NaH (6.43 g, 160.80 mmol, 60percent in mineral oil) and stirred for 1.5 h at 0° C.
After the addition of benzyl bromide (13.75 g, 80.40 mmol), the reaction mixture was warmed to room temperature and stirred overnight.
The solvent was evaporated under reduced pressure and the residue was dissolved in H2O.
The crude product was partitioned between H2O and Et2O.
The aqueous phase was acidified to pH<4 with 3 N HCl and extracted with EtOAc three times.
The combined EtOAc solution was washed with H2O, dried with Na2SO4, filtered, and concentrated to give the N-tert-butoxycarbonyl-O-benzyl-L-serine (17.27 g, 80percent).
75%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at -15℃; for 2 h;
Stage #2: at -15 - 20℃;
To a stirring solution of 2S-Z (50 g, 245 mmol) in DMF (650 mL) was added NaH (60percent) (23 g, 563 mmol) at -15 °C and stirred for 2 h. Benzyl bromide (32.8 mL, 269 mmol) was slowly added. The reaction mixture temperature was warmed to RT and stirred for 12 h. After consumption of the starting material (by TLC), the reaction mixture was poured into chilled water (200 mL) and extracted with diethylether (2x 250 mL). The aqueous layer was acidified with citric acid (pH~4) and extracted with EtOAc (2x500 mL). The combined organic layers were washed with water (3x250 mL). The organic extracts were dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to afford 2S-AA (54 g, 75percent) as brown syrup. H-NMR: (400 MHz, CDC13): δ 7.32-7.26 (m, 5H), 5.43 (d, J = 7.6 Hz, 1H), 4.70-4.46 (m, 1H), 4.45 (s, 2H), 4.13-3.91 (m, 1H), 3.73-3.70 (m, 1H), 1.44 (s, 9H).
75%
Stage #1: at -15℃; for 2 h;
Stage #2: at 20 - 25℃; for 12 h;
To a stirring solution of Int A (50 g, 245 mmol) in DMF (650 mL) was added NaH (60percent) (23 g, 563 mmol) at -15 °C and stirred for 2 h. After adding benzyl bromide (32.8 mL, 269 mmol) slowly, the reaction mixture was warmed to RT and stirred for 12 h. After consumption of the starting material (by TLC), the reaction mixture was poured into chilled water (200 mL) and extracted with diethylether (2x 250 mL). The aqueous layer was acidified with citric acid (pH~4) and extracted with EtOAc (2x500 mL). The combined organic layers were washed with water (3 x 250 mL). The organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford Int B (54 g, 75percent) as a brown syrup. (0569) 1H NMR: (400 MHz, CDCl3): δ 7.32-7.26 (m, 5H), 5.43 (d, J = 7.6 Hz, 1H), 4.70-4.46 (m, 1H), 4.45 (s, 2H), 4.13-3.91 (m, 1H), 3.73-3.70 (m, 1H), 1.44 (s, 9H)

Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 26, p. 3225 - 3229
[2] Patent: US2004/121316, 2004, A1,
[3] Patent: US2005/239054, 2005, A1,
[4] Patent: WO2014/120783, 2014, A1, . Location in patent: Paragraph 00145
[5] Patent: WO2018/26763, 2018, A1, . Location in patent: Page/Page column 81
[6] Journal of Medicinal Chemistry, 2010, vol. 53, # 11, p. 4545 - 4549
[7] Patent: WO2011/69149, 2011, A2, . Location in patent: Page/Page column 25-26
  • 7
  • [ 69871-79-0 ]
  • [ 23680-31-1 ]
Reference: [1] Tetrahedron, 1998, vol. 54, # 46, p. 13981 - 13996
[2] Journal of Organic Chemistry, 2005, vol. 70, # 22, p. 8730 - 8733
[3] Journal of Organic Chemistry, 1998, vol. 63, # 22, p. 7990 - 7992
[4] Advanced Synthesis and Catalysis, 2017, vol. 359, # 13, p. 2269 - 2279
  • 8
  • [ 24424-99-5 ]
  • [ 4726-96-9 ]
  • [ 23680-31-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 15, p. 1799 - 1804
[2] Nucleosides and Nucleotides, 1999, vol. 18, # 8, p. 1845 - 1861
[3] Organic Syntheses, 1985, vol. 63, p. 160 - 160
[4] Bioorganic and medicinal chemistry letters, 2004, vol. 14, # 1, p. 275 - 278
  • 9
  • [ 2712-78-9 ]
  • [ 23680-31-1 ]
Reference: [1] Patent: US6355660, 2002, B1,
  • 10
  • [ 4726-96-9 ]
  • [ 98015-52-2 ]
  • [ 23680-31-1 ]
Reference: [1] Synthesis, 1986, # 8, p. 627 - 632
  • 11
  • [ 3262-72-4 ]
  • [ 620-05-3 ]
  • [ 23680-31-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 26, p. 4524 - 4534
  • 12
  • [ 24424-99-5 ]
  • [ 23680-31-1 ]
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 26, p. 3225 - 3229
[2] Patent: WO2014/120783, 2014, A1,
[3] Patent: WO2018/26763, 2018, A1,
  • 13
  • [ 30200-52-3 ]
  • [ 23680-31-1 ]
Reference: [1] Chemical and pharmaceutical bulletin, 1987, vol. 35, # 2, p. 468 - 478
  • 14
  • [ 1070-19-5 ]
  • [ 4726-96-9 ]
  • [ 23680-31-1 ]
Reference: [1] Chemische Berichte, 1964, vol. 97, p. 2497 - 2503
  • 15
  • [ 23680-31-1 ]
  • [ 79069-15-1 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 19, p. 6726 - 6735
[2] Tetrahedron Letters, 1995, vol. 36, # 8, p. 1223 - 1226
[3] Journal of Organic Chemistry, 1981, vol. 46, # 23, p. 4799 - 4800
[4] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 9, p. 1119 - 1122
[5] Journal of Organic Chemistry, 1981, vol. 46, # 23, p. 4797 - 4798
[6] Tetrahedron Letters, 1993, vol. 34, # 41, p. 6513 - 6516
[7] Journal of Organic Chemistry, 1996, vol. 61, # 20, p. 6994 - 6996
[8] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 15, p. 1799 - 1804
[9] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 6, p. 1486 - 1490
[10] Synthetic Communications, 1996, vol. 26, # 13, p. 2511 - 2522
[11] Synthesis, 1990, p. 299 - 301
[12] Patent: WO2011/69149, 2011, A2, . Location in patent: Page/Page column 26
[13] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 2, p. 702 - 713
[14] Tetrahedron Letters, 2012, vol. 53, # 26, p. 3225 - 3229
[15] Tetrahedron Letters, 2012, vol. 53, # 32, p. 4216 - 4220
[16] Synlett, 2013, vol. 24, # 6, p. 747 - 751
  • 16
  • [ 23680-31-1 ]
  • [ 541-41-3 ]
  • [ 79069-15-1 ]
Reference: [1] Patent: EP1679296, 2006, A1, . Location in patent: Page/Page column 29
  • 17
  • [ 23680-31-1 ]
  • [ 543-27-1 ]
  • [ 79069-15-1 ]
YieldReaction ConditionsOperation in experiment
82% With sodium tetrahydroborate; triethanolamine In tetrahydrofuran; water; ethyl acetate N-(tert-Butyloxycarbonyl)-O-Benzyl-L-Serinol (3)
N-(tert-butyloxycarbonyl)-O- benzyl-L-serine 2 (6.0 g, 20.34 mmol) was dissolved in dry THF and cooled to -20° C. under argon atmosphere.
To this cold stirred solution was added TEA (2.32 g, 23 mmol) and isobutyl chloroformate (3.13 g, 23 mmol).
The stirring was continued for 30 min at -20° C. under argon atmosphere.
The reaction mixture was filtered immediately under a blanket of argon, the precipitate was washed with dry THF (50 ml).
The combined filtrate was added slowly into a cold (0° C.) solution of NaBH4 (7.4 g, 200 mmol) in THF/water (80:20, 200 ml) during 10 min period.
After the addition, the reaction mixture was stirred for 2 h at 0° C. and the pH adjusted to 7 with acetic acid.
The solution was evaporated to dryness, partitioned between ethyl acetate/water (300:150 ml) and extracted in ethyl acetate.
The organic extract was washed with brine (100 ml), dried over anhydrous sodium sulfate and evaporated to dryness.
The crude product was purified by flash column chromatography over silica gel using CH2 Cl2 -->EtOAc as the eluent.
The pure product was pooled together and evaporated to dryness to give 4.7 g (82percent) of the pure product as an oil. 1 H-NMR (CDCl3): δ1.41 (s, 9H, Boc), 3.60-3.70 (m, 4H), 3.82 (d, 2H), 4.53 (s, 2H, OCH2 Ph), 5.20 (bs, 1H, NH) and 7.30-7.40 (m, 5H, Ph).
Reference: [1] Patent: US5969135, 1999, A,
  • 18
  • [ 23680-31-1 ]
  • [ 19525-87-2 ]
YieldReaction ConditionsOperation in experiment
100% With thionyl chloride In dichloromethane at 0℃; for 14 h; Example 44A; <n="114"/>To a solution of 300 mg (1.02 mmol) (S)-3-benzyloxy-2-tert-butoxycarbonylamino- propionic acid in 10 ml DCM is added 1.5 ml (20.5 mmol) thionylchloride at 00C. After stirring for 14 h the mixture is concentrated and evaporated several times after the additon of methanol to yield the hydrochlorde of the product as a solid. yield: 270 mg (100percent)LC-MS (Method 1s): RT = 0.92 minMS (ESI pos): m/z = 210 (M+H)+
Reference: [1] Patent: WO2009/92566, 2009, A1, . Location in patent: Page/Page column 112-113
  • 19
  • [ 4530-20-5 ]
  • [ 15761-38-3 ]
  • [ 13734-34-4 ]
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  • [ 18942-46-6 ]
  • [ 54613-99-9 ]
  • [ 13139-14-5 ]
  • [ 65420-40-8 ]
  • [ 38916-34-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 17, p. 5981 - 5987
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