Alternatived Products of [ 473806-21-2 ]
Product Details of [ 473806-21-2 ]
CAS No. : 473806-21-2
MDL No. : MFCD08704530
Formula :
C11 H20 N2 O4
Boiling Point :
-
Linear Structure Formula : -
InChI Key : QOJVDTYOYUAFQA-SFYZADRCSA-N
M.W :
244.29
Pubchem ID : 22872214
Synonyms :
Calculated chemistry of [ 473806-21-2 ]
Physicochemical Properties
Num. heavy atoms :
17
Num. arom. heavy atoms :
0
Fraction Csp3 :
0.82
Num. rotatable bonds :
6
Num. H-bond acceptors :
5.0
Num. H-bond donors :
2.0
Molar Refractivity :
65.39
TPSA :
76.66 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) :
-7.33 cm/s
Lipophilicity
Log Po/w (iLOGP) :
2.45
Log Po/w (XLOGP3) :
0.65
Log Po/w (WLOGP) :
0.03
Log Po/w (MLOGP) :
0.22
Log Po/w (SILICOS-IT) :
0.17
Consensus Log Po/w :
0.7
Druglikeness
Lipinski :
0.0
Ghose :
None
Veber :
0.0
Egan :
0.0
Muegge :
0.0
Bioavailability Score :
0.55
Water Solubility
Log S (ESOL) :
-1.37
Solubility :
10.5 mg/ml ; 0.0428 mol/l
Class :
Very soluble
Log S (Ali) :
-1.84
Solubility :
3.57 mg/ml ; 0.0146 mol/l
Class :
Very soluble
Log S (SILICOS-IT) :
-1.61
Solubility :
5.94 mg/ml ; 0.0243 mol/l
Class :
Soluble
Medicinal Chemistry
PAINS :
0.0 alert
Brenk :
1.0 alert
Leadlikeness :
1.0
Synthetic accessibility :
3.22
Safety of [ 473806-21-2 ]
Application In Synthesis of [ 473806-21-2 ]
* 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 [ 473806-21-2 ]
Downstream synthetic route of [ 473806-21-2 ]
1
[ 20924-05-4 ]
[ 473806-21-2 ]
[ 189215-91-6 ]
Yield Reaction Conditions Operation in experiment
With hydrogenchloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine Yield given;
Reference:
[1]Jordan, Stephan; Schwemler, Christoph; Kosch, Winfried; Kretschmer, Axel; Schwenner, Eckhardt; Stropp, Udo; Mielke, Burkhard
[Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 6, p. 681 - 686]
2
[ 144564-95-4 ]
[ 473806-21-2 ]
[ 189215-92-7 ]
Yield Reaction Conditions Operation in experiment
With hydrogenchloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine Yield given;
Reference:
[1]Jordan, Stephan; Schwemler, Christoph; Kosch, Winfried; Kretschmer, Axel; Schwenner, Eckhardt; Stropp, Udo; Mielke, Burkhard
[Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 6, p. 681 - 686]
3
[ 189215-90-5 ]
[ 473806-21-2 ]
Yield Reaction Conditions Operation in experiment
98%
With methanol; palladium on activated charcoal
With hydrogen
Reference:
[1]Umashankara; Babu, I Ramesh; Ganesh, Krishna N
[Chemical Communications, 2003, # 20, p. 2606 - 2607]
[2]Jordan, Stephan; Schwemler, Christoph; Kosch, Winfried; Kretschmer, Axel; Schwenner, Eckhardt; Stropp, Udo; Mielke, Burkhard
[Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 6, p. 681 - 686]
4
[ 28920-43-6 ]
[ 473806-21-2 ]
[ 273222-06-3 ]
5
[ 64187-48-0 ]
[ 473806-21-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: 60 percent / PPh3 ; DIAD / tetrahydrofuran
2: 90 percent / NaN3 / dimethylformamide
3: 93 percent / H2 ; Ni / ethyl acetate
4: 98 percent / methanol; Pd/C
Multi-step reaction with 7 steps
1: 94 percent / PPh3 , DEAD
2: NaOMe / methanol
3: pyridine
4: 97 percent / LiN3
5: H2 S / pyridine
6: DIEA
7: H2 / Pd/C
Reference:
[1]Umashankara; Babu, I Ramesh; Ganesh, Krishna N
[Chemical Communications, 2003, # 20, p. 2606 - 2607]
[2]Jordan, Stephan; Schwemler, Christoph; Kosch, Winfried; Kretschmer, Axel; Schwenner, Eckhardt; Stropp, Udo; Mielke, Burkhard
[Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 6, p. 681 - 686]
6
[ 189215-89-2 ]
[ 473806-21-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 93 percent / H2 ; Ni / ethyl acetate
2: 98 percent / methanol; Pd/C
Multi-step reaction with 3 steps
1: H2 S / pyridine
2: DIEA
3: H2 / Pd/C
Reference:
[1]Umashankara; Babu, I Ramesh; Ganesh, Krishna N
[Chemical Communications, 2003, # 20, p. 2606 - 2607]
[2]Jordan, Stephan; Schwemler, Christoph; Kosch, Winfried; Kretschmer, Axel; Schwenner, Eckhardt; Stropp, Udo; Mielke, Burkhard
[Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 6, p. 681 - 686]
7
[ 51-35-4 ]
[ 473806-21-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: 98 percent / NaHCO3 / H2 O
2: 94 percent / SOCl2
3: 60 percent / PPh3 ; DIAD / tetrahydrofuran
4: 90 percent / NaN3 / dimethylformamide
5: 93 percent / H2 ; Ni / ethyl acetate
6: 98 percent / methanol; Pd/C
8
[ 13504-85-3 ]
[ 473806-21-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: 94 percent / SOCl2
2: 60 percent / PPh3 ; DIAD / tetrahydrofuran
3: 90 percent / NaN3 / dimethylformamide
4: 93 percent / H2 ; Ni / ethyl acetate
5: 98 percent / methanol; Pd/C
9
[ 77345-53-0 ]
[ 473806-21-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 90 percent / NaN3 / dimethylformamide
2: 93 percent / H2 ; Ni / ethyl acetate
3: 98 percent / methanol; Pd/C
10
[ 24424-99-5 ]
[ 473806-21-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: DIEA
2: H2 / Pd/C
Reference:
[1]Jordan, Stephan; Schwemler, Christoph; Kosch, Winfried; Kretschmer, Axel; Schwenner, Eckhardt; Stropp, Udo; Mielke, Burkhard
[Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 6, p. 681 - 686]
11
[ 57653-35-7 ]
[ 473806-21-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: pyridine
2: 97 percent / LiN3
3: H2 S / pyridine
4: DIEA
5: H2 / Pd/C
Reference:
[1]Jordan, Stephan; Schwemler, Christoph; Kosch, Winfried; Kretschmer, Axel; Schwenner, Eckhardt; Stropp, Udo; Mielke, Burkhard
[Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 6, p. 681 - 686]
12
[ 473806-21-2 ]
[ 185304-25-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: HOBt, EDC, HCl, Et3 N
2: 91 percent / LiOH / H2 O; dioxane
Reference:
[1]Jordan, Stephan; Schwemler, Christoph; Kosch, Winfried; Kretschmer, Axel; Schwenner, Eckhardt; Stropp, Udo; Mielke, Burkhard
[Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 6, p. 681 - 686]
13
[ 473806-21-2 ]
(2S,4R)-1-[2-(4-Benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-4-tert-butoxycarbonylamino-pyrrolidine-2-carboxylic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: HOBt, EDC, HCl, Et3 N
2: 93 percent / LiOH / H2 O; dioxane
Reference:
[1]Jordan, Stephan; Schwemler, Christoph; Kosch, Winfried; Kretschmer, Axel; Schwenner, Eckhardt; Stropp, Udo; Mielke, Burkhard
[Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 6, p. 681 - 686]
14
[ 762233-34-1 ]
[ 473806-21-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: DIEA
2: H2 / Pd/C
Reference:
[1]Jordan, Stephan; Schwemler, Christoph; Kosch, Winfried; Kretschmer, Axel; Schwenner, Eckhardt; Stropp, Udo; Mielke, Burkhard
[Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 6, p. 681 - 686]
15
[ 189215-88-1 ]
[ 473806-21-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: 97 percent / LiN3
2: H2 S / pyridine
3: DIEA
4: H2 / Pd/C
Reference:
[1]Jordan, Stephan; Schwemler, Christoph; Kosch, Winfried; Kretschmer, Axel; Schwenner, Eckhardt; Stropp, Udo; Mielke, Burkhard
[Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 6, p. 681 - 686]
16
[ 189215-87-0 ]
[ 473806-21-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: NaOMe / methanol
2: pyridine
3: 97 percent / LiN3
4: H2 S / pyridine
5: DIEA
6: H2 / Pd/C
Reference:
[1]Jordan, Stephan; Schwemler, Christoph; Kosch, Winfried; Kretschmer, Axel; Schwenner, Eckhardt; Stropp, Udo; Mielke, Burkhard
[Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 6, p. 681 - 686]
17
EDCl*HCl
[ No CAS ]
HOBT*H2 O
[ No CAS ]
[ 20924-05-4 ]
[ 473806-21-2 ]
4-tert-Butyloxycarbonylamino-N-[(thymin-1-yl)-acetyl]-L-cis-proline methyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
With sodium hydrogencarbonate; triethylamine; sodium chloride In hydrogenchloride; ethyl acetate; N,N-dimethyl-formamide
28 4-tert-Butyloxycarbonylamino-N-[(thymin-1-yl)-acetyl]-L-trans-proline methyl ester
Example 28 4-tert-Butyloxycarbonylamino-N-[(thymin-1-yl)-acetyl]-L-trans-proline methyl ester 275 mg (1.5 mmol) of 1-carboxy-methylthymine are dissolved in 10 ml of abs. DMF, cooled to -30° C., and 230 mg (1.7 mmol) of HOBT*H2 O and 330 mg (1.7 mmol) of EDCL*HCl are added at this temperature. The mixture is then subsequently stirred at -30° C. for 15 min, and a suspension of 245 mg (1 mmol) of 4-tertbutyloxycarbonylamino-L-trans-proline methyl ester in 10 ml of DMF and 0.41 ml (3 mmol) of triethylamine is added at -30° C. The mixture is stirred at -30° C. for one hour and subsequently placed at room temperature for 24 h. It is then concentrated and the residue taken up in ethyl acetate and extracted in turn with 1 N HCl, a saturated solution of NaHCO3 and a saturated solution of NaCl. The organic phase is dried over Na2 SO4, filtered and concentrated. Yield: 300 mg (73.1% of theory) Rf: 0,16, eluent, toluene/EtOH (8:1)