HRID1524850

反应详情

EQUATION

反应方程式

REACTANTS

反应物

$结构：CO[C@H]1C[C@@H]2CC[C@@H](C)[C@@](O)(O2)C(=O)C(=O)N2CCCC[C@H]2C(=O)O[C@H]([C@H](C)C[C@@H]2CC[C@@H](O)[C@H](OC)C2)CC(=O)[C@H](C)/C=C(\C)[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)/C=C/C=C/C=C/1C$

HCID5284616

Sirolimus

C51H79NO13

结构：CC(C)(C)[Si](C)(C)OCCOS(=O)(=O)C(F)(F)F

HCID15678107

2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl trifluoromethanesulfonate

C9H19F3O4SSi

PRODUCTS

生成物

$结构：CO[C@H]1C[C@@H]2CC[C@@H](C)[C@@](O)(O2)C(=O)C(=O)N2CCCC[C@H]2C(=O)O[C@H]([C@H](C)C[C@@H]2CC[C@@H](OCCO)[C@H](OC)C2)CC(=O)[C@H](C)/C=C(\C)[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)/C=C/C=C/C=C/1C$

HCID6442177

Everolimus

C53H83NO14

PROCEDURE

实验过程

Accordingly, the present disclosure relates to a process for obtaining Everolimus, said process comprising acts of a) adding 2-(-t-butyldimethylsilyl)oxyethyl triflate (2) to Sirolimus to obtain crude 40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin (3) and b) treating and purifying the crude 40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin (3) to obtain Everolimus; a process for obtaining Everolimus, said process comprising acts of a) adding Sirolimus to 2-(-t-butyldimethylsilyl)oxyethyl triflate (2) to obtain crude 40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin (3) and b) treating and purifying the crude 40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin (3) to obtain Everolimus; a process for obtaining Everolimus, said process comprising acts of a) obtaining a mixture comprising Sirolimus, 2-(t-butyldimethylsilyl)ethylene glycol (1), base and organic solvent, in any order thereof, b) adding 2-(-t-butyldimethylsilyl)oxyethyl triflate (2) to the mixture to obtain crude 40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin (3) and c) treating and purifying the crude 40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin (3) to obtain Everolimus; and a process for obtaining Everolimus, said process comprising acts of a) obtaining a mixture comprising 2-(-t-butyldimethylsilyl)oxyethyl triflate (2), 2-(t-butyldimethylsilyl)ethylene glycol (1), base and organic solvent, in any order thereof, b) adding Sirolimus to the mixture to obtain crude 40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin (3) and c) treating and purifying the crude 40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin (3) to obtain Everolimus.

WORKUP

后处理

customto obtain crude 40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin (3) and b)
additiontreating
custompurifying the crude 40-O-[2-(t-butyldimethylsilyl)oxy]ethyl rapamycin (3)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-9d352a65d179441d93691aa14ccf4952
来源数据集: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09079921B2
来源说明: uspto-grants-2015_07

反应 SMILES

[CH3:1][C@H:2]1[C@@:41]2([OH:43])[O:42][C@H:5]([CH2:6][C@H:7]([O:64][CH3:65])[C:8]([CH3:63])=[CH:9][CH:10]=[CH:11][CH:12]=[CH:13][C@@H:14]([CH3:62])[CH2:15][C@@H:16]([CH3:61])[C:17]([C@H:19]([O:59][CH3:60])[C@H:20]([OH:58])[C:21]([CH3:57])=[CH:22][C@@H:23]([CH3:56])[C:24]([CH2:26][C@@H:27]([C@@H:44]([CH2:46][C@H:47]3[CH2:52][C@@H:51]([O:53][CH3:54])[C@H:50]([OH:55])[CH2:49][CH2:48]3)[CH3:45])[O:28][C:29]([C@H:31]3[N:36]([C:37]([C:39]2=[O:40])=[O:38])[CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:30])=[O:25])=[O:18])[CH2:4][CH2:3]1.[O:66]([CH2:74][CH2:75]O[Si](C(C)(C)C)(C)C)S(C(F)(F)F)(=O)=O>>[CH3:1][C@H:2]1[C@@:41]2([OH:43])[O:42][C@H:5]([CH2:6][C@H:7]([O:64][CH3:65])[C:8]([CH3:63])=[CH:9][CH:10]=[CH:11][CH:12]=[CH:13][C@@H:14]([CH3:62])[CH2:15][C@@H:16]([CH3:61])[C:17]([C@H:19]([O:59][CH3:60])[C@H:20]([OH:58])[C:21]([CH3:57])=[CH:22][C@@H:23]([CH3:56])[C:24]([CH2:26][C@@H:27]([C@@H:44]([CH2:46][C@H:47]3[CH2:52][C@@H:51]([O:53][CH3:54])[C@H:50]([O:55][CH2:75][CH2:74][OH:66])[CH2:49][CH2:48]3)[CH3:45])[O:28][C:29]([C@H:31]3[N:36]([C:37]([C:39]2=[O:40])=[O:38])[CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:30])=[O:25])=[O:18])[CH2:4][CH2:3]1