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【结 构 式】

【分子编号】51091

【品名】(2S)-3-chloro-2-hydroxypropyl 3-nitrobenzenesulfonate

【CA登记号】

【 分 子 式 】C9H10ClNO6S

【 分 子 量 】295.70024

【元素组成】C 36.56% H 3.41% Cl 11.99% N 4.74% O 32.46% S 10.84%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(IX)

In this scheme various methods are shown for the synthesis of (S)-atenolol: 1. Treatment of (R)-glycidyl 4-nitrobenzenesulfonate (I) with HCl (either concentrated or with dichloromethane) provides 3-chloropropyl derivative (II), which is then coupled with isopropylamine (III) in dichloromethane to afford 3-chloropropylisopropylamine (IV). Finally, condensation of (IV) with 2-(4-hydroxyphenyl)acetamide (V) by means of KOH in MeOH gives the desired product. Alternatively, derivative (IV) can be converted into (S)-atenolol by its condensation with 2-(4-hydroxy-phenyl)acetonitrile (VI) by means of KOH to yield compound (VII), followed by hydrolysis with HCl at 40 C. 2. Condensation of (R)-glycidyl 3-nitrobenzenesulfonate (VIII) with isopropylamine (III) followed by coupling with acetamide (V) by means of potassium tert-butylate in DMSO provides the desired product. 3. Treatment of (VIII) with HCl affords 2(S)-hydroxy-3-chloropropyl-3-nitrobenzenesulfonate (IX), which is first coupled with isopropylamine (III) to give (IV) and finally condensed with amide (V). 4. Coupling of chloro derivative (IX) with benzyl-protected isopropylamine (X) provides protected derivative (XI), which is then condensed with acetamide (V) by means of KOH in MeOH to give (XII). Finally, compound (XII) is hydrogenated over Pd/C in MeOH for removal of the benzyl group.

1 Westfelt, A.; Andersson, L.; Birgersson, B.; Westfelt, L.; Process for preparing homochiral amines and process for preparing intermediates for the preparation thereof, and the intermediates prepared in accordance with this process. WO 9110642 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 45631 (2S)oxiranylmethyl 4-nitrobenzenesulfonate C9H9NO6S 详情 详情
(II) 51089 (2S)-3-chloro-2-hydroxypropyl 4-nitrobenzenesulfonate C9H10ClNO6S 详情 详情
(III) 23933 2-Propanamine; Isopropylamine 75-31-0 C3H9N 详情 详情
(IV) 51090 (2S)-1-chloro-3-(isopropylamino)-2-propanol C6H14ClNO 详情 详情
(V) 32754 p-Hydroxyphenylacetamide; 2-(4-hydroxyphenyl)acetamide; 4-Hydroxybenzeneacetamide; 4-Hydroxyphenylacetamide 17194-82-0 C8H9NO2 详情 详情
(VI) 32753 2-(4-hydroxyphenyl)acetonitrile; 4-Hydroxybenzyl cyanide 14191-95-8 C8H7NO 详情 详情
(VII) 51088 2-(4-[[(2S)-2-hydroxy-3-(isopropylamino)propyl]oxy]phenyl)acetonitrile C14H20N2O2 详情 详情
(VIII) 16259 (2S)oxiranylmethyl 3-nitrobenzenesulfonate; (S)-(+)-Glycidyl nosylate 115314-14-2 C9H9NO6S 详情 详情
(IX) 51091 (2S)-3-chloro-2-hydroxypropyl 3-nitrobenzenesulfonate C9H10ClNO6S 详情 详情
(X) 39750 N-benzyl-N-isopropylamine; N-benzyl-2-propanamine 102-97-6 C10H15N 详情 详情
(XI) 51092 (2S)-1-[benzyl(isopropyl)amino]-3-chloro-2-propanol C13H20ClNO 详情 详情
(XII) 51093 2-[4-([(2S)-3-[benzyl(isopropyl)amino]-2-hydroxypropyl]oxy)phenyl]acetamide C21H28N2O3 详情 详情
Extended Information