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CAS No. : | 3519-30-0 | MDL No. : | MFCD04972376 |
Formula : | C9H18O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XQTIFSCLEWPKCF-ZETCQYMHSA-N |
M.W : | 174.24 | Pubchem ID : | 12943847 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With dmap; dicyclohexyl-carbodiimide In dichloromethane for 24h; Ambient temperature; | |
(i) PhSO2Cl, Py, (ii) /BRN= 4658890/; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With pyridine In dichloromethane at 0℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With dimethyl amine In methanol at 0℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With dmap; dicyclohexyl-carbodiimide In dichloromethane for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With water; potassium carbonate In methanol at 0℃; for 2h; | tert-Butyl (S)-2-hydroxy-3-methylbutanoate (10) To a solution of ester 9 (1.32 g, 7.58 mmol) in MeOH (2 mL) was added a solution ofK2CO3 (2.90 g, 21.0 mmol) in H2O/MeOH (20 mL, 7:5) dropwise at 0 C. After 2 h, thereaction mixture was diluted with H2O and extracted with CH2Cl2 (x 5). The combinedorganic layers was dried over MgSO4. Concentrated in vacuo afforded 10 as colorlessoil (970 mg, 5.57 mmol, 73%). [α]D = +1.2 (c 2.12, MeOH), (lit a, [α]D = +1.6 (c 0.01,MeOH)); [α]D = +7.5 (c 1.13, CHCl3), (R)-isomer : (lit b, [α]D = -4.4 (c 0.31, CHCl3)); 1H NMR (300 MHz, CDCl3) δ 3.91 (1H, dd, J = 5.9, 3.3 Hz), 2.75 (1H, d, J = 5.9 Hz),2.10-1.95 (1H, m), 1.50 (9H, s), 1.02 (3H, d, J = 6.9 Hz), 0.86 (3H, d, J = 6.9 Hz);LR-ESI-MS m/z 175 [M+H]+. |
With lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 3h; | ||
With lithium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 3h; |
With potassium carbonate In methanol; water at 20℃; for 12h; | ||
With ethylenediamine In cyclohexane at 90℃; for 18h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0℃; for 5h; | |
With thiamine diphosphate; diethylazodicarboxylate In tetrahydrofuran at 0℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 84 percent / 18 h / 20 °C 2: toluene / 3 h / 95 °C 3: LiOH / H2O; methanol; tetrahydrofuran / 3 h / 20 °C | ||
Multi-step reaction with 3 steps 1: 18 h / 20 °C 2: toluene / 3 h / 95 °C 3: aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C | ||
Multi-step reaction with 3 steps 1: 4 h / 60 °C 2: DMAP; DCC / CH2Cl2 / 12 h / 20 °C 3: K2CO3 / methanol; H2O / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene / 3 h / 95 °C 2: LiOH / H2O; methanol; tetrahydrofuran / 3 h / 20 °C | ||
Multi-step reaction with 2 steps 1: toluene / 3 h / 95 °C 2: aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C | ||
Multi-step reaction with 2 steps 1: DMAP; DCC / CH2Cl2 / 12 h / 20 °C 2: K2CO3 / methanol; H2O / 12 h / 20 °C |
Multi-step reaction with 2 steps 1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 0 - 20 °C 2: potassium carbonate; water / methanol / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature 7: 70 percent / DCC, dimethylaminopyridine / CH2Cl2 / 15 h / Ambient temperature | ||
Multi-step reaction with 7 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 98 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature 7: 70 percent / DCC, dimethylaminopyridine / CH2Cl2 / 15 h / Ambient temperature | ||
Multi-step reaction with 7 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature 7: 70 percent / DCC, dimethylaminopyridine / CH2Cl2 / 15 h / Ambient temperature |
Multi-step reaction with 7 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 98 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature 7: 70 percent / DCC, dimethylaminopyridine / CH2Cl2 / 15 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature | ||
Multi-step reaction with 2 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2, citric acid / Pd / methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C | ||
Multi-step reaction with 4 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 98 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr | ||
Multi-step reaction with 4 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 98 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 84 percent / dimethylaminopyridine, DCC / CH2Cl2 / 20 h 2: 100 percent / TFA / CH2Cl2 / 5 h / Ambient temperature 3: 86 percent / dimethylaminopyridine, DCC / CH2Cl2 / 84 h / 0 °C 4: 99 percent / H2, AcOH / 10percent Pd/C / ethyl acetate / 9 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature | ||
Multi-step reaction with 3 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 84 percent / dimethylaminopyridine, DCC / CH2Cl2 / 20 h 2: 100 percent / TFA / CH2Cl2 / 5 h / Ambient temperature 3: 76 percent / dimethylaminopyridine, DCC / CH2Cl2 / 17 h / 0 °C 4: 93 percent / H2, AcOH / 10percent Pd/C / ethyl acetate / 13 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C 5: 62 percent / DCC, dimethylaminopyridine / CH2Cl2 / 12 h / Ambient temperature | ||
Multi-step reaction with 5 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C 5: 62 percent / DCC, dimethylaminopyridine / CH2Cl2 / 12 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature 7: 70 percent / DCC, dimethylaminopyridine / CH2Cl2 / 15 h / Ambient temperature 8: 5 percent / H2, dimethylaminopyridine / 5percent Pd/C / dioxane; ethanol / 90 °C | ||
Multi-step reaction with 8 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 98 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature 7: 70 percent / DCC, dimethylaminopyridine / CH2Cl2 / 15 h / Ambient temperature 8: 5 percent / H2, dimethylaminopyridine / 5percent Pd/C / dioxane; ethanol / 90 °C | ||
Multi-step reaction with 8 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature 7: 70 percent / DCC, dimethylaminopyridine / CH2Cl2 / 15 h / Ambient temperature 8: 5 percent / H2, dimethylaminopyridine / 5percent Pd/C / dioxane; ethanol / 90 °C |
Multi-step reaction with 8 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 98 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature 7: 70 percent / DCC, dimethylaminopyridine / CH2Cl2 / 15 h / Ambient temperature 8: 5 percent / H2, dimethylaminopyridine / 5percent Pd/C / dioxane; ethanol / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature | ||
Multi-step reaction with 6 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 98 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature | ||
Multi-step reaction with 6 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature |
Multi-step reaction with 6 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 98 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature | ||
Multi-step reaction with 5 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 98 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature | ||
Multi-step reaction with 5 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature |
Multi-step reaction with 5 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 98 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 84 percent / dimethylaminopyridine, DCC / CH2Cl2 / 20 h 2: 100 percent / TFA / CH2Cl2 / 5 h / Ambient temperature 3: 86 percent / dimethylaminopyridine, DCC / CH2Cl2 / 84 h / 0 °C 4: 99 percent / H2, AcOH / 10percent Pd/C / ethyl acetate / 9 h / Ambient temperature 5: 55 percent / dimethylaminopyridine, DCC / CH2Cl2 / 72 h / 0 °C 6: 97 percent / TFA / CH2Cl2 / 7.5 h / Ambient temperature | ||
Multi-step reaction with 6 steps 1: 84 percent / dimethylaminopyridine, DCC / CH2Cl2 / 20 h 2: 100 percent / TFA / CH2Cl2 / 5 h / Ambient temperature 3: 86 percent / dimethylaminopyridine, DCC / CH2Cl2 / 84 h / 0 °C 4: 99 percent / TFA / CH2Cl2 / 6 h / Ambient temperature 5: 55 percent / dimethylaminopyridine, DCC / CH2Cl2 / 72 h / 0 °C 6: 97 percent / TFA / CH2Cl2 / 7.5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 84 percent / dimethylaminopyridine, DCC / CH2Cl2 / 20 h 2: 100 percent / TFA / CH2Cl2 / 5 h / Ambient temperature 3: 86 percent / dimethylaminopyridine, DCC / CH2Cl2 / 84 h / 0 °C 4: 99 percent / H2, AcOH / 10percent Pd/C / ethyl acetate / 9 h / Ambient temperature 5: 55 percent / dimethylaminopyridine, DCC / CH2Cl2 / 72 h / 0 °C | ||
Multi-step reaction with 5 steps 1: 84 percent / dimethylaminopyridine, DCC / CH2Cl2 / 20 h 2: 100 percent / TFA / CH2Cl2 / 5 h / Ambient temperature 3: 86 percent / dimethylaminopyridine, DCC / CH2Cl2 / 84 h / 0 °C 4: 99 percent / TFA / CH2Cl2 / 6 h / Ambient temperature 5: 55 percent / dimethylaminopyridine, DCC / CH2Cl2 / 72 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd / methanol; acetic acid | ||
Multi-step reaction with 2 steps 1: PhSO2Cl / pyridine 2: H2 / Pd-C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid | ||
Multi-step reaction with 2 steps 1: PhSO2Cl, Py 2: H2 / PdCl2-C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (i) Py, PhSO2Cl, (ii) /BRN= 4658890/ 2: H2 / Pd | ||
Multi-step reaction with 2 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2, AcOH / PdO / methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: (i) Py, PhSO2Cl, (ii) /BRN= 4658890/ 2: H2 / Pd 3: (i) PCl5, (ii) /BRN= 2418531/, Et3N 4: H2 / Pd | ||
Multi-step reaction with 4 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2, AcOH / PdO / methanol 3: (i) PCl5, Et2O, (ii) /BRN= 2418531/, Et3N 4: H2, HCl / PdO / methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: (i) Py, PhSO2Cl, (ii) /BRN= 4658890/ 2: H2 / Pd 3: (i) Et3N, ClCO2Et, (ii) /BRN= 6132110/ 4: CF3CO2H 5: (i) PCl5, (ii) /BRN= 6133284/, Et3N 6: HBr / acetic acid | ||
Multi-step reaction with 6 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / PdO / methanol 3: (i) ClCO2Et, Et3N, THF, (ii) /BRN= 6132110/ 4: HCl / diethyl ether 5: (i) PCl5, Et2O, (ii) /BRN= 6133284/, Et3N, THF 6: HBr / acetic acid / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: (i) Py, PhSO2Cl, (ii) /BRN= 4658890/ 2: H2 / Pd 3: (i) Et3N, ClCO2Et, (ii) /BRN= 6132110/ | ||
Multi-step reaction with 3 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / PdO / methanol 3: (i) ClCO2Et, Et3N, THF, (ii) /BRN= 6132110/ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: (i) Py, PhSO2Cl, (ii) /BRN= 4658890/ 2: H2 / Pd 3: (i) PCl5, (ii) /BRN= 2418531/, Et3N | ||
Multi-step reaction with 3 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2, AcOH / PdO / methanol 3: (i) PCl5, Et2O, (ii) /BRN= 2418531/, Et3N |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: TsOH / benzene 3: (i) SOCl2, (ii) /BRN= 2417866/, Et3N, benzene 4: H2 / Pd / methanol 5: (i) SOCl2, (ii) /BRN= 2633973/, Et3N, benzene 6: CF3CO2H | ||
Multi-step reaction with 6 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: TsOH / benzene 3: (i) SOCl2, (ii) /BRN= 2417866/, Et3N, benzene 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 2633973/, Et3N, benzene 6: CF3CO2H |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: TsOH / benzene 3: (i) SOCl2, (ii) /BRN= 2417867/, Et3N, benzene 4: H2 / Pd / methanol 5: (i) SOCl2, (ii) /BRN= 2633974/, Et3N, benzene 6: CF3CO2H | ||
Multi-step reaction with 6 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: TsOH / benzene 3: (i) SOCl2, (ii) /BRN= 2417867/, Et3N, benzene 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 2633974/, Et3N, benzene 6: CF3CO2H |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: TsOH / benzene 3: (i) SOCl2, (ii) /BRN= 2417866/, Et3N, benzene 4: H2 / Pd / methanol 5: (i) SOCl2, (ii) /BRN= 2633973/, Et3N, benzene | ||
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: TsOH / benzene 3: (i) SOCl2, (ii) /BRN= 2417866/, Et3N, benzene 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 2633973/, Et3N, benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: TsOH / benzene 3: (i) SOCl2, (ii) /BRN= 2417867/, Et3N, benzene 4: H2 / Pd / methanol 5: (i) SOCl2, (ii) /BRN= 2633974/, Et3N, benzene | ||
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: TsOH / benzene 3: (i) SOCl2, (ii) /BRN= 2417867/, Et3N, benzene 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 2633974/, Et3N, benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: (i) carbonyldiimidazole, CH2Cl2, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) SOCl2, (ii) /BRN= 6700597/, Et3N, Et2O | ||
Multi-step reaction with 5 steps 1: (i) carbonyldiimidazole, CH2Cl2, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) SOCl2, (ii) /BRN= 6700597/, Et3N, Et2O 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 6700597/, Et3N, Et2O |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF 4: CF3CO2H | ||
Multi-step reaction with 4 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: CF3CO2H 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF 4: CF3CO2H |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF 4: CF3CO2H | ||
Multi-step reaction with 4 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: CF3CO2H 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF 4: CF3CO2H |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF | ||
Multi-step reaction with 3 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: CF3CO2H 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF | ||
Multi-step reaction with 3 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: CF3CO2H 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 2418093/, Et3N, Et2O | ||
Multi-step reaction with 3 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) SOCl2, (ii) /BRN= 2418093/, Et3N, Et2O |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) SOCl2, (ii) /BRN= 2418093/, Et3N, Et2O | ||
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: CF3CO2H 3: (i) PCl5, Et2O, (ii) /BRN= 2809877/, Et3N, THF 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 2418093/, Et3N, Et2O |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 2809877/, Et3N, Et2O | ||
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: CF3CO2H 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 2809877/, Et3N, Et2O |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (i) Py, PhSO2Cl, (ii) /BRN= 4658890/ 2: H2 / Pd | ||
Multi-step reaction with 2 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / PdO / methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) SOCl2, (ii) /BRN= 6699841/, Et3N, Et2O 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 6699841/, Et3N, Et2O | ||
Multi-step reaction with 3 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) SOCl2, (ii) /BRN= 6699841/, Et3N, Et2O | ||
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: CF3CO2H 3: (i) SOCl2, (ii) /BRN= 6699841/, Et3N, Et2O 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 6699841/, Et3N, Et2O |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / PdO / methanol 3: (i) ClCO2Et, Et3N, THF, (ii) /BRN= 6132110/ 4: HCl / diethyl ether 5: (i) PCl5, Et2O, (ii) /BRN= 6133284/, Et3N, THF |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / PdO / methanol 3: (i) ClCO2Et, Et3N, THF, (ii) /BRN= 6132110/ 4: HCl / diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In tetrahydrofuran; diethyl ether | 1.A (S)-2-(chlorocarbamoyloxy)-3-methylbutyric acid, tert-butyl ester Method A (S)-2-(chlorocarbamoyloxy)-3-methylbutyric acid, tert-butyl ester To a solution of diphosgene (4.55 g) in THF (34 ml) at 0° C. was added a solution of (S)-2-hydroxy-3-methylbutyric acid tert-butyl ester (for preparation method see Tetrahedron. Lett., (1993), 7409) (4.0 g) and pyridine (1.82 g)in THF (34 ml) dropwise over 25 minutes. The resulting mixture was allowed to warm to room temperature over 4 hours. The mixture was then filtered through celite and the filtrate concentrated under reduced pressure. The residue was re-dissolved in diethyl ether (200 ml) and again filtered through celite. The filtrate was concentrated under reduced pressure to give the sub-title compound as a pale yellow oil (5.27 g): 1H NMR (400 MHz, CDCl3) δ 0.98-1.10 (6H, m), 1.55 (9H, s), 2.30 (1H, m), 4.83 (1H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With 2,6-dimethylpyridine In dichloromethane at 0℃; for 0.833333h; Inert atmosphere; optical yield given as %ee; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; | (S)-1-(tert-Butoxy)-3-methyl-1-oxobutan-2-yl N-((benzyloxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-threoninate (12) To a mixture of alcohol 10 (799 mg, 4.59 mmol), 11 (2.02 g, 5.51 mmol) and DMAP(167 mg, 1.38 mmol) in CH2Cl2 (18 mL) was added a solution of DCC (1.25 g, 6.06mmol) in CH2Cl2 (18 mL) dropwise at 0 C. The reaction mixture was stirred overnightat rt. The reaction mixture was diluted with n-hexane. The resulting mixture was filteredthrough a pad of Celite and concentrated in vacuo. The crude residue was purified byflash column chromatography (7% EtOAc in n-hexane) to give compound 12 ascolorless oil (2.24 g, 4.28 mmol, 93%). [α]D = -23.4 (c 1.1, CHCl3); 1H NMR (300 MHz,CDCl3) δ 7.45-7.30 (5H, m), 5.45 (1H, d, J = 9.6 Hz), 5.14 (2H, s), 4.82 (1H, d, J =4.2Hz), 4.50 (1H, qd, J = 6.2, 2.0 Hz), 4.31 (1H, dd, J = 9.6, 2.0 Hz), 2.25-2.12 (1H, m),1.46 (9H, s), 1.25 (3H, d, J = 6.2 Hz), 0.98 (3H, d, J = 7.0 Hz), 0.96 (3H, d, J = 7.0 Hz),0.83 (9H, s), 0.06 (3H, s), 0.03 (3H, s); 13C NMR (75 MHz, CDCl3) δ 170.53, 167.85,156.49, 136.24, 128.45, 128.13, 128.09, 81.85, 77.24, 68.40, 66.96, 59.70, 30.33, 27.92,25.65, 21.24, 18.60, 17.78, 17.04, -4.55, -5.24; HR-ESI-MS calcd. for C27H46NO7Si524.3038: found 524.3038 [M+H]+. |
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