Alternatived Products of [ 210345-89-4 ]
Product Details of [ 210345-89-4 ]
CAS No. : 210345-89-4
MDL No. : MFCD07372885
Formula :
C7 H15 NO2
Boiling Point :
-
Linear Structure Formula : -
InChI Key : IAXQYBCPMFDMOJ-ZCFIWIBFSA-N
M.W :
145.20
Pubchem ID : 11355546
Synonyms :
Calculated chemistry of [ 210345-89-4 ]
Physicochemical Properties
Num. heavy atoms :
10
Num. arom. heavy atoms :
0
Fraction Csp3 :
0.86
Num. rotatable bonds :
4
Num. H-bond acceptors :
3.0
Num. H-bond donors :
2.0
Molar Refractivity :
40.24
TPSA :
63.32 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) :
-8.44 cm/s
Lipophilicity
Log Po/w (iLOGP) :
1.31
Log Po/w (XLOGP3) :
-1.77
Log Po/w (WLOGP) :
0.69
Log Po/w (MLOGP) :
0.75
Log Po/w (SILICOS-IT) :
0.25
Consensus Log Po/w :
0.25
Druglikeness
Lipinski :
0.0
Ghose :
None
Veber :
0.0
Egan :
0.0
Muegge :
1.0
Bioavailability Score :
0.55
Water Solubility
Log S (ESOL) :
0.64
Solubility :
632.0 mg/ml ; 4.35 mol/l
Class :
Highly soluble
Log S (Ali) :
0.96
Solubility :
1310.0 mg/ml ; 9.03 mol/l
Class :
Highly soluble
Log S (SILICOS-IT) :
-0.55
Solubility :
40.6 mg/ml ; 0.28 mol/l
Class :
Soluble
Medicinal Chemistry
PAINS :
0.0 alert
Brenk :
0.0 alert
Leadlikeness :
1.0
Synthetic accessibility :
1.55
Safety of [ 210345-89-4 ]
Application In Synthesis of [ 210345-89-4 ]
* 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 [ 210345-89-4 ]
Downstream synthetic route of [ 210345-89-4 ]
2
[ 82911-69-1 ]
[ 210345-89-4 ]
[ 1018899-99-4 ]
Reference:
[1] Tetrahedron Asymmetry, 2008, vol. 19, # 24, p. 2839 - 2849
[2] Journal of Organic Chemistry, 2003, vol. 68, # 4, p. 1575 - 1578
[3] Chemistry and Biodiversity, 2012, vol. 9, # 11, p. 2494 - 2506
1
[ 191664-13-8 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
With hydrogenchloride; lithium hydroxide; dihydrogen peroxide 2) aq. HOAc; Multistep reaction;
Multi-step reaction with 2 steps
1: 76 percent / H2 O2 , LiOH*H2 O / H2 O; tetrahydrofuran / 1 h / 0 °C
2: 65 percent / aq. HCl / acetic acid / 48 h / Heating
Reference:
[1]Hintermann, Tobias; Seebach, Dieter
[Synlett, 1997, # SPEC. ISS., p. 437 - 438]
[2]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
2
[ 104-15-4 ]
[ 210345-89-4 ]
[ 100-51-6 ]
benzyl (2R)-2-aminomethyl4methylpentanoate toluenesulfonate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
86%
In benzene for 9h; Heating;
Reference:
[1]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
3
[ 210345-88-3 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
86%
With hydrogenchloride In acetic acid at 110℃;
65%
With hydrogenchloride In acetic acid for 48h; Heating;
Reference:
[1]Coffey; Drauz; Roberts; Skidmore; Smith
[Chemical Communications, 2001, # 22, p. 2330 - 2331]
[2]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
4
[ 218285-68-8 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
With hydrogen In methanol Yield given;
5
[ 28920-43-6 ]
[ 210345-89-4 ]
[ 1018899-99-4 ]
6
[ 82911-69-1 ]
[ 210345-89-4 ]
[ 1018899-99-4 ]
7
[ 501330-99-0 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
With ammonium formate In methanol at 60℃;
8
[ 927830-83-9 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
With lithium hydroxide In water
9
[ 24424-99-5 ]
[ 210345-89-4 ]
(R)-2-[(tert-butoxycarbonyl)amino]methyl}-4-methylpentanoic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
2.3 g
With potassium carbonate In 1,4-dioxane for 5h;
10
[ 887143-13-7 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 64 percent / zinc; dibromoethane / tetrahydrofuran / 1.5 h / 20 °C
2: Pd/C; ammonium formate / tetrahydrofuran; methanol / 20 °C
3: LiOH / H2 O
11
[ 887143-14-8 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: Pd/C; ammonium formate / tetrahydrofuran; methanol / 20 °C
2: LiOH / H2 O
12
[ 61-90-5 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1.1: 70 percent / sodium bromide; sodium nitrite; aq. H2 SO4 / H2 O / 7 h / 0 - 20 °C
2.1: isobutyl chloroformate; N-methylmorpholine / 1,2-dimethoxy-ethane / 0.25 h / -15 °C
2.2: 61 percent / NaH / 1,2-dimethoxy-ethane / 2 h / -15 - 20 °C
3.1: 64 percent / zinc; dibromoethane / tetrahydrofuran / 1.5 h / 20 °C
4.1: Pd/C; ammonium formate / tetrahydrofuran; methanol / 20 °C
5.1: LiOH / H2 O
13
[ 28659-87-2 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1.1: isobutyl chloroformate; N-methylmorpholine / 1,2-dimethoxy-ethane / 0.25 h / -15 °C
1.2: 61 percent / NaH / 1,2-dimethoxy-ethane / 2 h / -15 - 20 °C
2.1: 64 percent / zinc; dibromoethane / tetrahydrofuran / 1.5 h / 20 °C
3.1: Pd/C; ammonium formate / tetrahydrofuran; methanol / 20 °C
4.1: LiOH / H2 O
14
[ 118053-31-9 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: triethylamine / dimethylformamide / 24 h / 20 °C
2: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C
3: HCOONH4 / 10percent Pd/C / methanol / 60 °C
15
[ 501330-86-5 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: 94 percent / LiHMDS / tetrahydrofuran / 6 h / 20 °C
2: triethylamine / dimethylformamide / 24 h / 20 °C
3: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C
4: HCOONH4 / 10percent Pd/C / methanol / 60 °C
16
2-[Hydroxy-((S)-1-phenyl-ethyl)-amino]-methyl}-4-methyl-pentanoic acid ethyl ester
[ No CAS ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C
2: HCOONH4 / 10percent Pd/C / methanol / 60 °C
17
[ 134806-81-8 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 53 percent / TiCl4 ; TEA / CH2 Cl2 / -10 °C
2: 82 percent / aq. H2 O2 ; LiOH / tetrahydrofuran / 0 °C
3: 86 percent / aq. HCl / acetic acid / 110 °C
18
[ 406949-04-0 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 82 percent / aq. H2 O2 ; LiOH / tetrahydrofuran / 0 °C
2: 86 percent / aq. HCl / acetic acid / 110 °C
19
[ 163810-26-2 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 7 steps
1: 1.) TiCl4 , (i-Pr)2NEt / 1.) CH2 Cl2 , 0 deg C, 1 h, 2.) CH2 Cl2 , 0 deg C, 6 h
2: H2 O2 , H2 O, LiOH / tetrahydrofuran / 1 h / 0 °C
3: H2 / 10percent Pd/C / methanol
4: NaOH, H2 O, EDCI / tetrahydrofuran / Ambient temperature
5: DEAD, Ph3 P / tetrahydrofuran / Ambient temperature
6: 100 percent / LiOH, H2 O / tetrahydrofuran; methanol / 0 °C
7: H2 / 10percent Pd/C / methanol
20
[ 218285-52-0 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: NaOH, H2 O, EDCI / tetrahydrofuran / Ambient temperature
2: DEAD, Ph3 P / tetrahydrofuran / Ambient temperature
3: 100 percent / LiOH, H2 O / tetrahydrofuran; methanol / 0 °C
4: H2 / 10percent Pd/C / methanol
21
[ 220805-34-5 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: H2 / 10percent Pd/C / methanol
2: NaOH, H2 O, EDCI / tetrahydrofuran / Ambient temperature
3: DEAD, Ph3 P / tetrahydrofuran / Ambient temperature
4: 100 percent / LiOH, H2 O / tetrahydrofuran; methanol / 0 °C
5: H2 / 10percent Pd/C / methanol
22
[ 218285-64-4 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 100 percent / LiOH, H2 O / tetrahydrofuran; methanol / 0 °C
2: H2 / 10percent Pd/C / methanol
23
[ 218285-60-0 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: DEAD, Ph3 P / tetrahydrofuran / Ambient temperature
2: 100 percent / LiOH, H2 O / tetrahydrofuran; methanol / 0 °C
3: H2 / 10percent Pd/C / methanol
24
(R)-4-Benzyl-3-((R)-2-benzyloxymethyl-4-methyl-pentanoyl)-oxazolidin-2-one
[ No CAS ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: H2 O2 , H2 O, LiOH / tetrahydrofuran / 1 h / 0 °C
2: H2 / 10percent Pd/C / methanol
3: NaOH, H2 O, EDCI / tetrahydrofuran / Ambient temperature
4: DEAD, Ph3 P / tetrahydrofuran / Ambient temperature
5: 100 percent / LiOH, H2 O / tetrahydrofuran; methanol / 0 °C
6: H2 / 10percent Pd/C / methanol
25
[ 113543-30-9 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 78 percent / TiCl4 , Et3 N / CH2 Cl2 / 60 h / 0 °C
2: 76 percent / H2 O2 , LiOH*H2 O / H2 O; tetrahydrofuran / 1 h / 0 °C
3: 65 percent / aq. HCl / acetic acid / 48 h / Heating
Multi-step reaction with 2 steps
1: TiCl4 , Et3 N
2: 1) LiOH, H2 O2 , 2) HCl / 2) aq. HOAc
Multi-step reaction with 4 steps
1.1: titanium tetrachloride / dichloromethane / 0 °C / Inert atmosphere
1.2: Mannich Aminomethylation / 0 °C / Inert atmosphere
1.3: Mannich Aminomethylation / 16 h / -80 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran; hexane / 0 °C / Inert atmosphere
2.2: 0 °C / Inert atmosphere
3.1: water; mercury(II) trifluoroacetate / tetrahydrofuran / 20 °C / Inert atmosphere
4.1: hydrogen; water; palladium 10% on activated carbon; acetic acid / methanol / 16 h / 750.08 Torr
Reference:
[1]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
[2]Hintermann, Tobias; Seebach, Dieter
[Synlett, 1997, # SPEC. ISS., p. 437 - 438]
[3]Van Der Knaap, Matthijs; Basalan, Fatih; Van De Mei, Henny C.; Busscher, Henk J.; Van Der Marel, Gijsbert A.; Overkleeft, Herman S.; Overhand, Mark
[Chemistry and biodiversity, 2012, vol. 9, # 11, p. 2494 - 2506]
26
[ 210345-89-4 ]
[ 191664-17-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 86 percent / benzene / 9 h / Heating
2: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
Reference:
[1]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
27
[ 210345-89-4 ]
[ 200400-95-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: 86 percent / benzene / 9 h / Heating
2: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
3: HCl / dioxane / 2 h / 20 °C
4: 74 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
5: 99 percent / H2 / Pd/C / methanol / 18 h
Reference:
[1]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
28
[ 210345-89-4 ]
[ 191664-18-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: 86 percent / benzene / 9 h / Heating
2: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
3: HCl / dioxane / 2 h / 20 °C
4: 74 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
Reference:
[1]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
29
[ 210345-89-4 ]
[ 191664-19-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: 86 percent / benzene / 9 h / Heating
2: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
3: HCl / dioxane / 2 h / 20 °C
4: 74 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
5: 99 percent / H2 / Pd/C / methanol / 18 h
6: 69 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
Multi-step reaction with 6 steps
1: 86 percent / benzene / 9 h / Heating
2: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
3: HCl / dioxane / 2 h / 20 °C
4: 74 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
5: HCl / dioxane / 2 h / 20 °C
6: 69 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
Reference:
[1]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
[2]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
30
[ 210345-89-4 ]
(R)-2-[((R)-3-{(R)-2-[((R)-2-[(R)-3-((R)-2-Aminomethyl-3-methyl-butyrylamino)-2-methyl-propionylamino]-methyl}-4-methyl-pentanoylamino)-methyl]-3-methyl-butyrylamino}-2-methyl-propionylamino)-methyl]-4-methyl-pentanoic acid; compound with trifluoro-acetic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 8 steps
1: 86 percent / benzene / 9 h / Heating
2: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
3: HCl / dioxane / 2 h / 20 °C
4: 74 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
5: 99 percent / H2 / Pd/C / methanol / 18 h
6: 69 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
7: CH2 Cl2 / 4.5 h / 20 °C
8: H2 / Pd/C / methanol / 18 h
Multi-step reaction with 8 steps
1: 86 percent / benzene / 9 h / Heating
2: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
3: HCl / dioxane / 2 h / 20 °C
4: 74 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
5: HCl / dioxane / 2 h / 20 °C
6: 69 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
7: CH2 Cl2 / 4.5 h / 20 °C
8: H2 / Pd/C / methanol / 18 h
Reference:
[1]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
[2]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
31
[ 210345-89-4 ]
(R)-2-[((R)-3-Amino-2-methyl-propionylamino)-methyl]-4-methyl-pentanoic acid benzyl ester; hydrochloride
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 86 percent / benzene / 9 h / Heating
2: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
3: HCl / dioxane / 2 h / 20 °C
Reference:
[1]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
32
[ 210345-89-4 ]
[ 210345-68-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: 86 percent / benzene / 9 h / Heating
2: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
3: HCl / dioxane / 2 h / 20 °C
4: 74 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
5: HCl / dioxane / 2 h / 20 °C
6: 77 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
Reference:
[1]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
33
[ 210345-89-4 ]
(R)-2-[(R)-3-((R)-2-Aminomethyl-3-methyl-butyrylamino)-2-methyl-propionylamino]-methyl}-4-methyl-pentanoic acid benzyl ester; hydrochloride
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: 86 percent / benzene / 9 h / Heating
2: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
3: HCl / dioxane / 2 h / 20 °C
4: 74 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
5: HCl / dioxane / 2 h / 20 °C
Reference:
[1]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
34
[ 210345-89-4 ]
(R)-2-[((R)-3-{(R)-2-[((2R,3R)-3-Amino-2-methyl-butyrylamino)-methyl]-3-methyl-butyrylamino}-2-methyl-propionylamino)-methyl]-4-methyl-pentanoic acid benzyl ester; hydrochloride
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 7 steps
1: 86 percent / benzene / 9 h / Heating
2: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
3: HCl / dioxane / 2 h / 20 °C
4: 74 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
5: HCl / dioxane / 2 h / 20 °C
6: 77 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
7: HCl / dioxane / 2 h / 20 °C
Reference:
[1]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
35
[ 210345-89-4 ]
[ 210345-69-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: 86 percent / benzene / 9 h / Heating
2: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
3: HCl / dioxane / 2 h / 20 °C
4: 74 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
5: 99 percent / H2 / Pd/C / methanol / 18 h
6: 48 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
Multi-step reaction with 8 steps
1: 86 percent / benzene / 9 h / Heating
2: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
3: HCl / dioxane / 2 h / 20 °C
4: 74 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
5: HCl / dioxane / 2 h / 20 °C
6: 77 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
7: HCl / dioxane / 2 h / 20 °C
8: 48 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
Reference:
[1]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
[2]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
36
[ 210345-89-4 ]
H-(R)-β2 -HVal-(R)-β2 -HAla-(R)-β2 -HLeu-(2R,3R)-β2,3 -HAla(α-Me)-(R)-β2 -HVal-(R)-β2 -HAla-(R)-β2 -HLeu-OH trifluoroacetate salt
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 8 steps
1: 86 percent / benzene / 9 h / Heating
2: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
3: HCl / dioxane / 2 h / 20 °C
4: 74 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
5: 99 percent / H2 / Pd/C / methanol / 18 h
6: 48 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
7: CH2 Cl2 / 2 h / 20 °C
8: H2 / Pd/C / methanol / 18 h
Multi-step reaction with 10 steps
1: 86 percent / benzene / 9 h / Heating
2: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
3: HCl / dioxane / 2 h / 20 °C
4: 74 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
5: HCl / dioxane / 2 h / 20 °C
6: 77 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
7: HCl / dioxane / 2 h / 20 °C
8: 48 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
9: CH2 Cl2 / 2 h / 20 °C
10: H2 / Pd/C / methanol / 18 h
Reference:
[1]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
[2]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
37
[ 210345-89-4 ]
(R)-2-[((R)-3-{(R)-2-[((R)-2-[(R)-3-((R)-2-Aminomethyl-3-methyl-butyrylamino)-2-methyl-propionylamino]-methyl}-4-methyl-pentanoylamino)-methyl]-3-methyl-butyrylamino}-2-methyl-propionylamino)-methyl]-4-methyl-pentanoic acid benzyl ester; compound with trifluoro-acetic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 7 steps
1: 86 percent / benzene / 9 h / Heating
2: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
3: HCl / dioxane / 2 h / 20 °C
4: 74 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
5: 99 percent / H2 / Pd/C / methanol / 18 h
6: 69 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
7: CH2 Cl2 / 4.5 h / 20 °C
Multi-step reaction with 7 steps
1: 86 percent / benzene / 9 h / Heating
2: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
3: HCl / dioxane / 2 h / 20 °C
4: 74 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
5: HCl / dioxane / 2 h / 20 °C
6: 69 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
7: CH2 Cl2 / 4.5 h / 20 °C
Reference:
[1]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
[2]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
38
[ 210345-89-4 ]
H-(R)-β2 -HVal-(R)-β2 -HAla-(R)-β2 -HLeu-(2R,3R)-β2,3 -HAla(α-Me)-(R)-β2 -HVal-(R)-β2 -HAla-(R)-β2 -HLeu-OBn trifluoroacetate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 7 steps
1: 86 percent / benzene / 9 h / Heating
2: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
3: HCl / dioxane / 2 h / 20 °C
4: 74 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
5: 99 percent / H2 / Pd/C / methanol / 18 h
6: 48 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
7: CH2 Cl2 / 2 h / 20 °C
Multi-step reaction with 9 steps
1: 86 percent / benzene / 9 h / Heating
2: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
3: HCl / dioxane / 2 h / 20 °C
4: 74 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
5: HCl / dioxane / 2 h / 20 °C
6: 77 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
7: HCl / dioxane / 2 h / 20 °C
8: 48 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.
9: CH2 Cl2 / 2 h / 20 °C
Reference:
[1]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
[2]Seebach, Dieter; Abele, Stefan; Gademann, Karl; Guichard, Gilles; Hintermann, Tobias; Jaun, Bernhard; Matthews, Jennifer L.; Schreiber, Juerg V.; Oberer, Lukas; Hommel, Ulrich; Widmer, Hans
[Helvetica Chimica Acta, 1998, vol. 81, # 5, p. 932 - 982]
39
[ 132606-01-0 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
92%
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 4h; enantioselective reaction;
40
[ 631899-15-5 ]
[ 210345-89-4 ]
[ 203854-56-2 ]
41
[ 1415986-78-5 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: water; mercury(II) trifluoroacetate / tetrahydrofuran / 20 °C / Inert atmosphere
2: hydrogen; water; palladium 10% on activated carbon; acetic acid / methanol / 16 h / 750.08 Torr
Reference:
[1]Van Der Knaap, Matthijs; Basalan, Fatih; Van De Mei, Henny C.; Busscher, Henk J.; Van Der Marel, Gijsbert A.; Overkleeft, Herman S.; Overhand, Mark
[Chemistry and biodiversity, 2012, vol. 9, # 11, p. 2494 - 2506]
42
[ 1415986-81-0 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
With palladium 10% on activated carbon; water; hydrogen; acetic acid In methanol for 16h;
Reference:
[1]Van Der Knaap, Matthijs; Basalan, Fatih; Van De Mei, Henny C.; Busscher, Henk J.; Van Der Marel, Gijsbert A.; Overkleeft, Herman S.; Overhand, Mark
[Chemistry and biodiversity, 2012, vol. 9, # 11, p. 2494 - 2506]
43
[ 1415986-75-2 ]
[ 210345-89-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 0 °C / Inert atmosphere
1.2: 0 °C / Inert atmosphere
2.1: water; mercury(II) trifluoroacetate / tetrahydrofuran / 20 °C / Inert atmosphere
3.1: hydrogen; water; palladium 10% on activated carbon; acetic acid / methanol / 16 h / 750.08 Torr
Reference:
[1]Van Der Knaap, Matthijs; Basalan, Fatih; Van De Mei, Henny C.; Busscher, Henk J.; Van Der Marel, Gijsbert A.; Overkleeft, Herman S.; Overhand, Mark
[Chemistry and biodiversity, 2012, vol. 9, # 11, p. 2494 - 2506]