* 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.
With potassium carbonate In tetrahydrofuran; water
To a solution of K2CO3 (0.75 g, 5. 43mmol), 3- (1-benzothien-3-yl)-L-alanine (1.0 g, 4.52 mmol) in THF:H2O (1: 1) was added (Boc) 20 (1.09 g, 5 mmol) at 0 C. The reaction mixture was then warmed up to RT and stirred overnight. Concentrated down the mixture and then dissolved into EtOAc and H20. The aqueous layer was adjusted to PH 1-2 by 6N HCI and the mixture was extracted with EtOAc three times. The organic layer was dried, filtered and concentrated to provide 1.22g product as a white foam (84percent).
Reference：
[1] Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 2090 - 2099
[2] Patent: WO2005/85227, 2005, A1, . Location in patent: Page/Page column 47; 117
2
[ 3216-47-5 ]
[ 154902-51-9 ]
Reference：
[1] Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 2090 - 2099
3
[ 63024-19-1 ]
[ 154902-51-9 ]
Reference：
[1] Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 2090 - 2099
4
[ 23906-20-9 ]
[ 154902-51-9 ]
Reference：
[1] Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 2090 - 2099
With potassium carbonate; In tetrahydrofuran; water;
To a solution of K2CO3 (0.75 g, 5. 43mmol), 3- (1-benzothien-3-yl)-L-alanine (1.0 g, 4.52 mmol) in THF:H2O (1: 1) was added (Boc) 20 (1.09 g, 5 mmol) at 0 C. The reaction mixture was then warmed up to RT and stirred overnight. Concentrated down the mixture and then dissolved into EtOAc and H20. The aqueous layer was adjusted to PH 1-2 by 6N HCI and the mixture was extracted with EtOAc three times. The organic layer was dried, filtered and concentrated to provide 1.22g product as a white foam (84%).
With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h;
D. N-[(1S)-1-(Benzo[b]thiophen-3-ylmethyl)-2-hydroxyethyl](tert-butoxy)carboxamide. N-<strong>[154902-51-9]Boc-L-3-benzothienylalanine</strong> (1 g, 3.1 mmol) was dissolved in THF (10 mL). Lithium aluminum hydride (237 mg, 6.2 mmol) was added to the THF solution in small portions and then allowed the reaction to stirred for 1 hour. The reaction was quenched with saturated aqueous Na2SO4 (2 mL), and then triturated in 2-propanol. The 2-propanol mixture was filtered and then concentrated to give a colorless oil, (0.75 g, 78% yield). MS (ESI) m/z 308.4 [M+1]+.
With BH3*THF; In tetrahydrofuran; at -10℃; for 3h;
To a solution of 107 (a) (1.22 g, 3.8 mmol) in THF at-10 C was added BH3. THF (22.8 ml, 22.8 mmol) dropwise. The reaction mixture was stirred at-10 C for 3hrs. Then mixture was concentrated down to one-third of the original volumn. Quenched with 9ml MeOH : acetic acid (9: 1). Concentrated down and the resultant was dissolved in EtOAc, washed by 1 N HCI, aqueous saturated NaHC03, brine, and dried over MgSO4. Concentrated down to provide 1.04g of the product as white solid.
<i>N</i>-{2-benzo[<i>b</i>]thiophen-3-yl-1-[4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl}-3-phenyl-2-phenylmethanesulfonylamino-propionamide[ No CAS ]
General procedure: A solution of (2S)-2-[(tert-butoxycarbonyl)amino]-3-(thiophen-2-yl)propanoicacid (compound 12f, 104.2 mg, 0.384 mmol) in DMF (5 mL) was addedHOBt (141.6 mg, 1.05 mmol) and EDCI (133.9 mg, 0.698 mmol). After stirring for30 min compound 20 (100 mg, 0.349mmol) and additional TEA (0.15 mL, 1.05 mmol) were added. This solution wasallowed to stir at room temperature for 20 h and then the saturated NaHCO3was added. The mixture was extracted with EtOAc and washed with saturated NaCl,dried over Na2SO4 and concentrated. The residue waspurified with flash chromatography on silica gel, eluted with a mixture ofPE/EA (4/1, v/v) to afford 21f (112 mg, 86%) as a white solid.
General procedure: Asolution of (2S)-2-[(tert-butoxycarbonyl)amino]-3-(furan-3-yl)propanoicacid (compound 12a, 105 mg, 0.410 mmol) in DMF (5 mL) was added HATU(283 mg, 0.745 mmol) and DIPEA (96 mg, 0.745 mmol). After stirring for 30 mincompound 11 (100 mg, 0.373 mmol) andadditional DIPEA were added. This solution was allowed to stir at roomtemperature for 20 h and then the saturated NaHCO3 was added. Themixture was extracted with EtOAc and washed with saturated NaCl, dried over Na2SO4and concentrated. The residue was purified with flash chromatography on silicagel, eluted with a mixture of PE/EA (4/1, v/v) to afford 13a (105 mg, 85%) as a white solid.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
