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[ CAS No. 1676-90-0 ] {[proInfo.proName]}

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Chemical Structure| 1676-90-0
Chemical Structure| 1676-90-0
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Product Details of [ 1676-90-0 ]

CAS No. :1676-90-0 MDL No. :MFCD00076912
Formula : C13H23NO6 Boiling Point : -
Linear Structure Formula :- InChI Key :PHJDCONJXLIIPW-QMMMGPOBSA-N
M.W : 289.32 Pubchem ID :7010636
Synonyms :
Boc-Asp(OtBu)-OH

Calculated chemistry of [ 1676-90-0 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.77
Num. rotatable bonds : 9
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 72.21
TPSA : 101.93 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) : -7.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.6
Log Po/w (XLOGP3) : 1.37
Log Po/w (WLOGP) : 1.7
Log Po/w (MLOGP) : 1.08
Log Po/w (SILICOS-IT) : 0.8
Consensus Log Po/w : 1.51

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.9
Solubility : 3.62 mg/ml ; 0.0125 mol/l
Class : Very soluble
Log S (Ali) : -3.11
Solubility : 0.223 mg/ml ; 0.00077 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.55
Solubility : 8.12 mg/ml ; 0.0281 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.44

Safety of [ 1676-90-0 ]

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 [ 1676-90-0 ]

* 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 [ 1676-90-0 ]
  • Downstream synthetic route of [ 1676-90-0 ]

[ 1676-90-0 ] Synthesis Path-Upstream   1~13

  • 1
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YieldReaction ConditionsOperation in experiment
100% With triethylamine In 1,4-dioxane; water 2.1. Preparation of Boc-Asp(O-tBu)-NCA (II-a)This method consisted in the cyclization of the free carboxylic acid with a main chain with one of the Bocs protecting the amine function, therefore first of all requiring the preparation of (Boc)2-Asp(O-t-Bu)-OH (VII-a). This was achieved by esterification of the α-carboxylic acid of Boc-Asp(O-t-Bu)-OH (V-a) into the benzyl ester (VI(a)), followed by a reaction with Boc2O in the presence of DMAP in order to give the amino compound protected by two Boc groups (VII-a), and then by deprotection of the benzyl ester group by hydrogenation in order to give (VIII-a). The following step consisted in the cyclization of the amino acid (VIII-a) protected with Vilsmeier's salt. The best results were obtained by forming the salt of DMF and oxalyl chloride in acetonitrile. The compound (II-a) was obtained with 90percent yield.
97%
Stage #1: at 0℃; for 0.0833333 h;
Stage #2: With sodium carbonate In tetrahydrofuran; water at 20℃; for 24 h;
General procedure: L-Aspartic acid 4-tert-butyl ester 4a (1.89 g, 10 mmol) was dissolved in a mixture of tetrahydrofuran (20 mL) and water (12 mL) at 0°C. After stirring for 5 minutes, di-tert-butyl dicarbonate (4.35 g, 2 eq.) was added in small portions followed by sodium carbonate (4.20 g, 4 eq.). The reaction was stirred at room temperature for 24 hours before evaporating the solvents under reduced pressure. The residue was dissolved in 10percent aqueous sodium hydrogen carbonate solution (50 mL), washed with diethyl ether (3 x 20 mL) and citric acid was added until pH 4.0 was reached. The product was extracted with ethyl acetate (3 x 100 mL) and the combined organic phases were dried over magnesium sulfate, filtered and evaporated to give pure 4-tert-butoxy-2-(tert-butoxycarbonylamino)-4-oxobutanoic acid 5a as a colourless oil (2.82 g, 97percent).
96% With sodium hydroxide In 1,4-dioxane; water (2S)-2-(tert-Butoxycarbonylamino)-4-tert-butoxy-4-oxo-butanoic acid is commercially available. The compound was prepared from commercial H-L-Asp(OtBu)-OH (5.68 g, 30.0 mmol) and Boc20 (6.55 g, 30.0 mmol) in a mixture of 1,4-dioxane (25 mL) and a freshly prepared 1.0 N aqueous sodium hydroxide (NaOH) solution (33 mL, 33 mmol) (8.33 g, 96percent yield) (Bowers, et al., J. Am. Chem Soc, 2009, 131(8), 2900-2905; and Keller, et al., Org. Synth., 1985, 63, 160). Colorless solid; m.p. : 47-53 °C; 1H NMR (300 MHz, CDCI3): δ 7.2-6.6 (br. s, 1H), 5.52 (d, J= 8.7 Hz, 1H), 4.62-4.50 (m, 1H), 2.94 (dd, J= 16.8, 4.2 Hz, 1H), 2.74 (dd, J= 16.8, 4.8 Hz, 1H), 1.45 (s, 9H, partially superimposed), 1.44 (s, 9H, partially superimposed) ppm; LC/MS: Rt = 1.645 min; ESI (pos.) m/z = 290.20 (M+H+)+, 601.00 (2M+Na+)+; ESI (neg.) m/z = 288.10 (M-H+)", 576.90 (2M-H+)~ The analytical data correspond to the analytical data obtained for the (S)-enantiomer (Example 5).
Reference: [1] Patent: US2010/16631, 2010, A1, . Location in patent: Page/Page column 5-6
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 4975 - 4978
[3] Patent: WO2017/24009, 2017, A1, . Location in patent: Paragraph 0652
[4] Russian Journal of Bioorganic Chemistry, 1999, vol. 25, # 5, p. 283 - 287[5] Bioorganicheskaya Khimiya, 1999, vol. 25, # 5, p. 323 - 328
  • 2
  • [ 1913-12-8 ]
  • [ 1676-90-0 ]
Reference: [1] Patent: US6750348, 2004, B1, . Location in patent: Page column 84-85
[2] Patent: EP1362856, 2003, A1, . Location in patent: Page/Page column 145
  • 3
  • [ 130074-09-8 ]
  • [ 1676-90-0 ]
Reference: [1] Chemistry of Natural Compounds, 1990, vol. 26, # 2, p. 196 - 198[2] Khimiya Prirodnykh Soedinenii, 1990, # 2, p. 241 - 245
  • 4
  • [ 566188-97-4 ]
  • [ 1676-90-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1964, vol. 673, p. 208 - 220
  • 5
  • [ 1070-19-5 ]
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Reference: [1] Justus Liebigs Annalen der Chemie, 1964, vol. 673, p. 208 - 220
  • 6
  • [ 2131-29-5 ]
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Reference: [1] Justus Liebigs Annalen der Chemie, 1964, vol. 673, p. 208 - 220
  • 7
  • [ 5545-52-8 ]
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Reference: [1] Tetrahedron, 1972, vol. 28, p. 2649 - 2654
[2] Chemische Berichte, 1972, vol. 105, # 11, p. 3650 - 3657
  • 8
  • [ 30750-74-4 ]
  • [ 1676-90-0 ]
Reference: [1] Chemistry of Natural Compounds, 1990, vol. 26, # 2, p. 196 - 198[2] Khimiya Prirodnykh Soedinenii, 1990, # 2, p. 241 - 245
  • 9
  • [ 130052-01-6 ]
  • [ 1676-90-0 ]
Reference: [1] Chemistry of Natural Compounds, 1990, vol. 26, # 2, p. 196 - 198[2] Khimiya Prirodnykh Soedinenii, 1990, # 2, p. 241 - 245
  • 10
  • [ 36702-55-3 ]
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Reference: [1] Chemische Berichte, 1972, vol. 105, # 11, p. 3650 - 3657
  • 11
  • [ 16965-08-5 ]
  • [ 3057-74-7 ]
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Reference: [1] Journal of the Chemical Society [Section] C: Organic, 1967, p. 2632 - 2636
  • 12
  • [ 1070-19-5 ]
  • [ 3057-74-7 ]
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Reference: [1] Helvetica Chimica Acta, 1963, vol. 46, p. 1975 - 1996
[2] Chemische Berichte, 1972, vol. 105, # 11, p. 3650 - 3657
[3] Tetrahedron, 1972, vol. 28, p. 2649 - 2654
  • 13
  • [ 1070-19-5 ]
  • [ 2673-19-0 ]
  • [ 1676-90-0 ]
Reference: [1] Hoppe-Seyler's Zeitschrift für physiologische Chemie, 1963, vol. 333, p. 108 - 113
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