Alternatived Products of [ 69557-34-2 ]
Product Details of [ 69557-34-2 ]
CAS No. : 69557-34-2
MDL No. : MFCD12796097
Formula :
C8 H17 NO2
Boiling Point : -
Linear Structure Formula : -
InChI Key : N/A
M.W : 159.23 g/molPubchem ID : -
Synonyms :
Calculated chemistry of of [ 69557-34-2 ]
Physicochemical Properties
Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.88
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.3
TPSA : 52.32 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) : -6.33 cm/s
Lipophilicity
Log Po/w (iLOGP) : 2.12
Log Po/w (XLOGP3) : 1.33
Log Po/w (WLOGP) : 0.92
Log Po/w (MLOGP) : 1.08
Log Po/w (SILICOS-IT) : 0.66
Consensus Log Po/w : 1.22
Druglikeness
Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55
Water Solubility
Log S (ESOL) : -1.4
Solubility : 6.32 mg/ml ; 0.0397 mol/l
Class : Very soluble
Log S (Ali) : -2.03
Solubility : 1.49 mg/ml ; 0.00933 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.25
Solubility : 8.97 mg/ml ; 0.0564 mol/l
Class : Soluble
Medicinal Chemistry
PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.93
Application In Synthesis of [ 69557-34-2 ]
* 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 [ 69557-34-2 ] Downstream synthetic route of [ 69557-34-2 ]
1
[ 64-17-5 ]
[ 33105-81-6 ]
[ 69557-34-2 ]
2
[ 51486-80-7 ]
[ 69557-34-2 ]
Yield Reaction Conditions Operation in experiment
With hydrogenchloride
3
[ 124-63-0 ]
[ 69557-34-2 ]
[ 191792-80-0 ]
Yield Reaction Conditions Operation in experiment
95%
With triethylamine In dichloromethane at 0℃; for 0.5h;
4
[ 69557-34-2 ]
[ 98-09-9 ]
[ 191792-81-1 ]
Yield Reaction Conditions Operation in experiment
95%
With triethylamine In dichloromethane at 0℃; for 0.5h;
5
[ 507229-71-2 ]
[ 69557-34-2 ]
[ 253178-21-1 ]
Yield Reaction Conditions Operation in experiment
With hydrogen In ethanol at 20℃; Title compound not separated from byproducts;
6
[ 62965-34-8 ]
[ 69557-34-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: Al / aq. ethanol
2: (i) HCl, (ii) (racemate resolution using (-)-dibenzoyl-tartaric acid)
7
C17 H27 FN5 O7 P
[ No CAS ]
[ 69557-34-2 ]
C23 H38 FN6 O8 P
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Stage #1: C17 H27 FN5 O7 P; ethyl (S)-2-amino-3,3-dimethylbutanoate With triethylamine In acetonitrile at 0℃; for 2h; Inert atmosphere;
Stage #2: With potassium carbonate In water; acetonitrile at 20℃; for 0.25h; Inert atmosphere;
22
To a solution of intermediate 18 (0.5 g, 1 eq) in P(O)(OEt)3 (Aldrich) (5 ml) at 0° C. under nitrogen was added dropwise POCl3 (Aldrich) (0.22 ml, 1.5 eq). The mixture was stirred at 0° C. during 1 hour. Intermediate 19 (0.36 g, 1.2 eq) in anhydrous acetonitrile (5 ml) was added dropwise, followed by addition of Et3N (1 ml, 4 eq) at 0° C. The reaction mixture was stirred at 0° C. for 2 hours. Water (10 ml) and K2CO3 (600 mg) were added and the mixture stirred at room temperature during 15 minutes, before addition of Na2SO4, filtration and evaporation under reduced pressure. The resulting residue was taken into anhydrous DMF (20 ml), followed by addition of DIEA (1 ml, 7 eq) and intermediate 20 (0.25 ml, 2 eq). The reaction mixture was stirred at 100° C. under microwave irradiations during 15 minutes and monitored by LC/MS. After two more additions of intermediate 20 (2×0.25 ml, 4 eq) and stirring 2×15 minutes at 100° C., the mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude mixture was purified by chromatography on silica gel column (eluent: CH2Cl2/CH3OH 0 to 10%) followed by purification on reverse phase column chromatography (eluent: water/CH3CN 0 to 100%). Finally, the 2 diastereoisomers 21 and 22 were separated by prepMS:
8
[ 64-17-5 ]
[ 20859-02-3 ]
[ 69557-34-2 ]
Yield Reaction Conditions Operation in experiment
69%
With thionyl chloride at 0 - 80℃;
22
To a solution of L-tert-leucine (1 g, 1 eq) in anhydrous ethanol (30 ml) was added, dropwise, at 0° C., thionylchloride (Aldrich) (2.8 ml, 5 eq). The reaction mixture was heated overnight at 80° C. The solvent was evaporated under reduced pressure. The resulting white powder was washed with petroleum ether, filtered and concentrated under reduced pressure to give the title intermediate as a white solid in 69% yield. 1H NMR (DMSO, 400 MHz) δ (ppm) 1.00 (s, 9H), 1.23 (m, 3H), 3.68 (s, 1H), 4.20 (m, 2H), 8.47 (m, 3H).
9
[ 69557-34-2 ]
ethyl (S)-2-acetamido-3,3-dimethyl-4-phenylbutanoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: acetic acid; palladium diacetate; trifluorormethanesulfonic acid; silver trifluoromethanesulfonate / 24 h / 100 °C / Sealed tube
2: triethylamine / dichloromethane / 0.08 h / 0 °C
Multi-step reaction with 2 steps
1: acetic acid; palladium diacetate; silver(I) acetate; trifluorormethanesulfonic acid / 24 h / 80 °C / Sealed tube
2: triethylamine / dichloromethane / 0.08 h / 0 °C
Reference：
[1]Yuan, Feipeng; Hou, Zhen-Lin; Pramanick, Pranab K.; Yao, Bo
[Organic Letters, 2019, vol. 21, # 23, p. 9381 - 9385]
[2]Yuan, Feipeng; Hou, Zhen-Lin; Pramanick, Pranab K.; Yao, Bo
[Organic Letters, 2019, vol. 21, # 23, p. 9381 - 9385]
10
[ 69557-34-2 ]
ethyl (S)-2-acetamido-3-benzyl-3-methyl-4-phenylbutanoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: acetic acid; palladium diacetate; trifluorormethanesulfonic acid; silver trifluoromethanesulfonate / 24 h / 100 °C / Sealed tube
2: triethylamine / dichloromethane / 0.08 h / 0 °C
Multi-step reaction with 2 steps
1: acetic acid; palladium diacetate; silver(I) acetate; trifluorormethanesulfonic acid / 24 h / 80 °C / Sealed tube
2: triethylamine / dichloromethane / 0.08 h / 0 °C
Reference：
[1]Yuan, Feipeng; Hou, Zhen-Lin; Pramanick, Pranab K.; Yao, Bo
[Organic Letters, 2019, vol. 21, # 23, p. 9381 - 9385]
[2]Yuan, Feipeng; Hou, Zhen-Lin; Pramanick, Pranab K.; Yao, Bo
[Organic Letters, 2019, vol. 21, # 23, p. 9381 - 9385]
11
[ 69557-34-2 ]
ethyl (S)-2-acetamido-3,3-dibenzyl-4-phenylbutanoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: acetic acid; palladium diacetate; silver(I) acetate; trifluorormethanesulfonic acid / 24 h / 80 °C / Sealed tube
2: triethylamine / dichloromethane / 0.08 h / 0 °C
12
[ 619-44-3 ]
[ 69557-34-2 ]
methyl (S)-4-(3-amino-4-ethoxy-2,2-dimethyl-4-oxobutyl)benzoate
[ No CAS ]
dimethyl 4,4'-(2-(1-amino-2-ethoxy-2-oxoethyl)-2-methylpropane-1,3-diyl)(S)-dibenzoate
[ No CAS ]
dimethyl 4,4'-(2-(1-amino-2-ethoxy-2-oxoethyl)-2-(4-(methoxycarbonyl)benzyl)propane-1,3-diyl)(S)-dibenzoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
1: 41%
2: 36%
3: 7%
With trifluorormethanesulfonic acid; silver(I) acetate; palladium diacetate; acetic acid at 80℃; for 24h; Sealed tube;
13
[ 619-44-3 ]
[ 69557-34-2 ]
methyl (S)-4-(3-acetamido-4-ethoxy-2,2-dimethyl-4-oxobutyl)benzoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: acetic acid; palladium diacetate; silver(I) acetate; trifluorormethanesulfonic acid / 24 h / 80 °C / Sealed tube
2: triethylamine / dichloromethane / 0.08 h / 0 °C
14
[ 696-62-8 ]
[ 69557-34-2 ]
ethyl (S)-2-amino-4-(4-methoxyphenyl)-3,3-dimethylbutanoate
[ No CAS ]
ethyl (S)-2-amino-3-(4-methoxybenzyl)-4-(4-methoxyphenyl)-3-methylbutanoate
[ No CAS ]
ethyl (S)-2-amino-3,3-bis(4-methoxybenzyl)-4-(4-methoxyphenyl)butanoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
1: 39%
2: 30%
3: 7%
With trifluorormethanesulfonic acid; silver(I) acetate; palladium diacetate; acetic acid at 80℃; for 24h; Sealed tube;
15
[ 352-34-1 ]
[ 69557-34-2 ]
ethyl (S)-2-amino-4-(4-fluorophenyl)-3,3-dimethylbutanoate
[ No CAS ]
ethyl (S)-2-amino-3-(4-fluorobenzyl)-4-(4-fluorophenyl)-3-methylbutanoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
1: 39%
2: 37%
With trifluorormethanesulfonic acid; silver(I) acetate; palladium diacetate; acetic acid at 80℃; for 24h; Sealed tube;
16
[ 624-31-7 ]
[ 69557-34-2 ]
ethyl (S)-2-amino-4-(p-tolyl)-3,3-dimethylbutanoate
[ No CAS ]
ethyl (S)-2-amino-3-(p-tolyl)-4-(p-tolyl)-3-methylbutanoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
1: 35%
2: 33%
With trifluorormethanesulfonic acid; silver(I) acetate; palladium diacetate; acetic acid at 80℃; for 24h; Sealed tube;
17
[ 645-00-1 ]
[ 69557-34-2 ]
ethyl (S)-2-amino-3,3-dimethyl-4-(3-nitrophenyl)butanoate
[ No CAS ]
ethyl (S)-2-amino-3-methyl-3-(3-nitrobenzyl)-4-(3-nitrophenyl)butanoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
1: 40%
2: 20%
With trifluorormethanesulfonic acid; silver(I) acetate; palladium diacetate; acetic acid at 80℃; for 24h; Sealed tube;
18
[ 766-85-8 ]
[ 69557-34-2 ]
ethyl (S)-2-amino-3,3-dimethyl-4-(3-methoxylphenyl)butanoate
[ No CAS ]
ethyl (S)-2-amino-3-methyl-3-(3-methoxylbenzyl)-4-(3-methoxylphenyl)butanoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
1: 35%
2: 33%
With trifluorormethanesulfonic acid; silver(I) acetate; palladium diacetate; acetic acid at 80℃; for 24h; Sealed tube;
19
[ 529-28-2 ]
[ 69557-34-2 ]
ethyl (S)-2-amino-3,3-dimethyl-4-(2-methoxylphenyl)butanoate
[ No CAS ]
ethyl (S)-2-amino-3-methyl-3-(2-methoxylbenzyl)-4-(2-methoxylphenyl)butanoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
1: 46%
2: 32%
With trifluorormethanesulfonic acid; silver(I) acetate; palladium diacetate; acetic acid at 80℃; for 24h; Sealed tube;
20
[ 69557-34-2 ]
ethyl (S)-2-((S)-2-((S)-2-amino-3-methylbutanamido)-3-methylbutanamido)-3,3-di-methylbutanoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: dicyclohexyl-carbodiimide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
2: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C
3: dicyclohexyl-carbodiimide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
4: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C
21
[ 69557-34-2 ]
C23 H43 N3 O6
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: dicyclohexyl-carbodiimide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
2: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C
3: dicyclohexyl-carbodiimide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
22
[ 69557-34-2 ]
C11 H22 N2 O3
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: dicyclohexyl-carbodiimide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
2: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C
23
[ 69557-34-2 ]
ethyl (S)-2-((S)-2-(4-iodobenzamido)propanamido)-3,3-dimethylbutanoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: dicyclohexyl-carbodiimide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
2: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C
3: dicyclohexyl-carbodiimide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
24
[ 69557-34-2 ]
ethyl (S)-2-((S)-2-amino-3-methylbutanamido)-3,3-dimethylbutanoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: dicyclohexyl-carbodiimide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
2: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C
25
[ 69557-34-2 ]
ethyl (S)-2-((2S,3S)-2-amino-3-methylpentanamido)-3,3-dimethylbutanoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: dicyclohexyl-carbodiimide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
2: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C
26
[ 69557-34-2 ]
ethyl (S)-2-((S)-2-amino-3-methylbutanamido)-3,3-dimethyl-4-phenylbutanoate
[ No CAS ]
ethyl (S)-2-((S)-2-amino-3-methylbutanamido)-3-benzyl-3-methyl-4-phenylbutanoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: dicyclohexyl-carbodiimide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
2: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C
3: palladium diacetate; silver(I) acetate; lithium trifluoromethanesulfonate / 2,2,2-trifluoroethanol / 24 h / 100 °C / Sealed tube
27
[ 69557-34-2 ]
ethyl (S)-2-((2S,3S)-2-((S)-2-amino-3-methylbutanamido)-3-methyl-4-phenylbutanamido)-3,3-dimethylbutanoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: dicyclohexyl-carbodiimide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
2: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C
3: dicyclohexyl-carbodiimide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
4: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C
5: palladium diacetate; silver(I) acetate; copper diacetate; lithium trifluoromethanesulfonate / 2,2,2-trifluoroethanol / 24 h / 100 °C / Sealed tube
28
[ 69557-34-2 ]
ethyl (S)-2-((S)-2-(4-((S)-3-((S)-2-amino-3-methylbutanamido)-4-(((S)-1-(((S)-1-ethoxy-3-methyl-1-oxobutan-2-yl)amino)-3,3-dimethyl-1-oxobutan-2-yl)amino)-2,2-dimethyl-4-oxobutyl)benzamido)propanamido)-3,3-dimethylbutanoate
[ No CAS ]
diethyl 2,2'-(((2S,2'S)-2,2'-((4,4'-(2-((5S,8S,11S,14S)-14-amino-8-(tert-butyl)-5-isopropyl-15-methyl-4,7,10,13-tetraoxo-3-oxa-6,9,12-triazahexadecan-11-yl)-2-methylpropane-1,3-diyl)bis(benzoyl))bis(azanediyl))bis(propanoyl))bis(azanediyl))(2S,2'S)-bis(3,3-dimethylbutanoate)
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: dicyclohexyl-carbodiimide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
2: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C
3: dicyclohexyl-carbodiimide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C
4: palladium diacetate; silver(I) acetate / 2,2,2-trifluoroethanol / 24 h / 100 °C / Sealed tube
29
[ 13139-16-7 ]
[ 69557-34-2 ]
C19 H36 N2 O5
[ No CAS ]
Yield Reaction Conditions Operation in experiment
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 12h;
30
[ 13734-41-3 ]
[ 69557-34-2 ]
C18 H34 N2 O5
[ No CAS ]
Yield Reaction Conditions Operation in experiment
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 12h;
31
[ 69557-34-2 ]
Boc-Tle-Val-OH
[ No CAS ]
C24 H45 N3 O6
[ No CAS ]
Yield Reaction Conditions Operation in experiment
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 12h;
32
[ 15761-38-3 ]
[ 69557-34-2 ]
C16 H30 N2 O5
[ No CAS ]
Yield Reaction Conditions Operation in experiment
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 12h;
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