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[ CAS No. 37736-82-6 ] {[proInfo.proName]}

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Chemical Structure| 37736-82-6
Chemical Structure| 37736-82-6
Structure of 37736-82-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 37736-82-6 ]

CAS No. :37736-82-6 MDL No. :MFCD00076896
Formula : C14H25NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :MSZQAQJBXGTSHP-NSHDSACASA-N
M.W : 271.35 Pubchem ID :10588189
Synonyms :
(S)-2-((tert-Butoxycarbonyl)amino)-3-cyclohexylpropanoic acid
Chemical Name :(S)-2-((tert-Butoxycarbonyl)amino)-3-cyclohexylpropanoic acid

Calculated chemistry of [ 37736-82-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.86
Num. rotatable bonds : 7
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 73.58
TPSA : 75.63 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.36 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.17
Log Po/w (XLOGP3) : 3.65
Log Po/w (WLOGP) : 2.93
Log Po/w (MLOGP) : 1.85
Log Po/w (SILICOS-IT) : 1.73
Consensus Log Po/w : 2.47

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.36
Solubility : 0.118 mg/ml ; 0.000437 mol/l
Class : Soluble
Log S (Ali) : -4.93
Solubility : 0.00321 mg/ml ; 0.0000118 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -2.1
Solubility : 2.18 mg/ml ; 0.00804 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.12

Safety of [ 37736-82-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 37736-82-6 ]

* 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 [ 37736-82-6 ]
  • Downstream synthetic route of [ 37736-82-6 ]

[ 37736-82-6 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 13734-34-4 ]
  • [ 37736-82-6 ]
Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 11, p. 1411 - 1414
[2] Journal of the American Chemical Society, 2015, vol. 137, # 29, p. 9250 - 9253
[3] Heterocycles, 1993, vol. 35, # 2, p. 737 - 754
[4] Angewandte Chemie, 1991, vol. 103, # 12, p. 1735 - 1737
[5] Journal of Organic Chemistry, 1996, vol. 61, # 26, p. 9564 - 9568
[6] Patent: US5217958, 1993, A,
[7] Patent: US4981843, 1991, A,
[8] Patent: US4885292, 1989, A,
[9] Patent: EP396065, 1990, A1,
  • 2
  • [ 24424-99-5 ]
  • [ 25528-71-6 ]
  • [ 37736-82-6 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With sodium hydroxide In tetrahydrofuran; water for 2 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water
Step 2. (S)-2-(tert-Butoxycarbonylamino)-3-cycIohexylpropanoic acid. To a solution of (S)-2-amino-3-cyclohexylpropanoic acid hydrochloride (118 g, 0.57 mol) in 0.5 N aq NaOH (1200 mL) was added a solution of BoC2O (137 g, 0.63 mol) in THF (600 mL) and the mixture was stirred for 2 h. After removing the organic solvent, the aqueous layer was washed with Et2O (2 x 400 mL). The aqueous layer was acidified to pH 5 by addition of 2 N aq HCl. The mixture was extracted with EtOAc (3 x 400 mL). The combined EtOAc extracts were washed with brine, dried over Na2SO4 and evaporated to give (S)-2-(tert- butoxycarbonylamino)-3-cyclohexylpropanoic acid (142 g, 92percent) as an oil. 1H NMR: 0.92 (m, IH); 1.09-1.30 (m, 3H), 1.52 (m, IH)5 1.48 (s, 9H), 1.51 (m, IH)3 1.66 (m, 5H), 1.78 (m, IH), 4.32 (m, IH)5 4.88 (m, IH)5 8.55-9.48 (brs, IH).
Reference: [1] Journal of Antibiotics, 1996, vol. 49, # 9, p. 909 - 920
[2] Patent: WO2007/117557, 2007, A2, . Location in patent: Page/Page column 91
[3] Patent: US5756763, 1998, A,
  • 3
  • [ 4530-18-1 ]
  • [ 37736-82-6 ]
Reference: [1] Patent: US4495178, 1985, A,
[2] Patent: US4603121, 1986, A,
  • 4
  • [ 24424-99-5 ]
  • [ 27527-05-5 ]
  • [ 37736-82-6 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 4, p. 873 - 875
[2] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 20, p. 2305 - 2309
[3] Tetrahedron, 1992, vol. 48, # 2, p. 307 - 318
[4] Bioorganic and medicinal chemistry letters, 2004, vol. 14, # 1, p. 275 - 278
  • 5
  • [ 63-91-2 ]
  • [ 37736-82-6 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 4, p. 873 - 875
[2] Tetrahedron, 1992, vol. 48, # 2, p. 307 - 318
[3] Patent: WO2007/117557, 2007, A2,
  • 6
  • [ 2018-61-3 ]
  • [ 37736-82-6 ]
Reference: [1] Journal of Antibiotics, 1996, vol. 49, # 9, p. 909 - 920
  • 7
  • [ 100400-96-2 ]
  • [ 37736-82-6 ]
Reference: [1] Journal of Antibiotics, 1996, vol. 49, # 9, p. 909 - 920
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