HRID1017809

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(OC)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O

HCID84029

Clarithromycin

C38H69NO13

2 次

结构：Cc1cc(O)cc2c1O[C@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)CC2

HCID92094

D-delta-Tocopherol

C27H46O2

3 次

HCID3033877

2,3-Dihydroxypropyl octanoate

C11H22O4

2 次

结构：Cc1c(C)c2c(c(C)c1OC(=O)CCC(=O)O)CC[C@@](C)(CCCC(C)CCCC(C)CC(C)C)O2

HCID44428588

未命名化合物

PRODUCTS

生成物

HCID44428588

未命名化合物

结构：CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCc2cc(O)ccc2O1

HCID58866062

(2R)-3,4-Dihydro-2-methyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol

C26H44O2

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID702

Ethanol

C2H6O

PROCEDURE

实验过程

Clarithromycin was obtained as the free base from Wockhardt (Delhi, India). Vitamin E Succinate (VESA) was obtained from Eastman (Freeport Tenn.). Capmul® MCM was obtained from Abitec (Janesville Wis.); Poloxamer® 407 (Pluronic® F-127) from BASF (Parsippany N.J.); PEG-400 from Spectrum Chemicals (Gardenia Calif.), and d-δ-tocopherol from Sigma Chemicals (St Louis MO). An oil phase consisting of d-δ-tocopherol and Capmul MCM was prepared using 2 parts of δ-tocopherol. Surfactant and clarithromycin were then added as shown in the table below. Dry ethanol was used to dissolve the components at 70° C. and the ethanol was then removed under vacuum. A clear amber oil resulted, but upon cooling, oblong, “casket-lid” crystals of clarithromycin were observed. A tocol-soluble ion pair of this compound was then produced by addition of a stoichiometric equivalent of Vitamin E succinate (VESA) as the free acid. On re-dissolution in ethanol and cooling no crystals formed. The clarithromycin was now sufficiently soluble in the tocopherol oil to allow subsequent preparation of the emulsion. The oil was then re-heated to 45° C. and degassed immediately prior to emulsification as described below.

WORKUP

后处理

customwas prepared
dissolutionto dissolve the components at 70° C.
customthe ethanol was then removed under vacuum
customA clear amber oil resulted
temperatureupon cooling

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-4560e163006149e48bfb73577bd2881e
来源数据集: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06479540B1
来源说明: uspto-grants-2002_11

反应 SMILES

[CH3:1][C:2]1[C:7]2[O:8][C@@:9]([CH2:13][CH2:14][CH2:15][CH:16]([CH2:18][CH2:19][CH2:20][CH:21]([CH2:23][CH:24]([CH3:26])[CH3:25])[CH3:22])[CH3:17])([CH3:12])[CH2:10][CH2:11][C:6]=2[C:5]([CH3:27])=[C:4]([O:28][C:29]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[O:30])[C:3]=1[CH3:36].CCCCCCCC(OCC(O)CO)=O.C[C:53]1[CH:58]=[C:57]([OH:59])[CH:56]=[C:55]2[CH2:60][CH2:61][C@:62]([CH2:65][CH2:66][CH2:67][C@@H:68]([CH2:70][CH2:71][CH2:72][C@@H:73]([CH2:75][CH2:76][CH2:77][CH:78]([CH3:80])[CH3:79])[CH3:74])[CH3:69])([CH3:64])[O:63][C:54]=12.CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@@](OC)(C)C2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@@](OC)(C)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@@]1(O)C>C(O)C>[CH3:74][C@H:73]([CH2:75][CH2:76][CH2:77][CH:78]([CH3:80])[CH3:79])[CH2:72][CH2:71][CH2:70][C@H:68]([CH2:67][CH2:66][CH2:65][C@@:62]1([CH3:64])[O:63][C:54]2[CH:53]=[CH:58][C:57]([OH:59])=[CH:56][C:55]=2[CH2:60][CH2:61]1)[CH3:69].[CH3:1][C:2]1[C:7]2[O:8][C@@:9]([CH2:13][CH2:14][CH2:15][CH:16]([CH2:18][CH2:19][CH2:20][CH:21]([CH2:23][CH:24]([CH3:25])[CH3:26])[CH3:22])[CH3:17])([CH3:12])[CH2:10][CH2:11][C:6]=2[C:5]([CH3:27])=[C:4]([O:28][C:29]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[O:30])[C:3]=1[CH3:36]