HRID1532405

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10868

Dicyclohexylcarbodiimide

C13H22N2

HCID86531

(+/-)-Mosher's acid

C10H9F3O3

$结构：C=CC[C@@H]1/C=C(\C)C[C@H](C)C[C@H](OC)[C@H]2O[C@@](O)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@H](/C(C)=C/[C@@H]3CC[C@@H](O)[C@H](OC)C3)[C@H](C)[C@@H](O)CC1=O)[C@H](C)C[C@@H]2OC$

HCID445643

Tacrolimus

C44H69NO12

PRODUCTS

生成物

结构：C=CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(OC(=O)C(OC)(c4ccccc4)C(F)(F)F)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC

HCID57224156

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID14284

N,N-Dimethylpyridin-4-amine

C7H10N2

溶剂HCID3283

Diethyl Ether

C4H10O

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

To a solution of (−)-2-trifluoromethyl-2-methoxy-2-phenylacetic acid (51 mg) in ethyl acetate (10 ml) was added at room temperature N,N′-dicyclohexylcarbodiimide (47 mg). After stirring for 1.5 hours at room temperature, then the FR-900506 substance (25.0 mg) and 4-(N,N-dimethylamino)-pyridine (11 mg) were added, followed by stirring at room temperature for 3.5 hours. The resulting solution was concentrated to provide a residue, which was taken up in diethyl ether and then washed successively with hydrochloric acid, an aqueous sodium hydrogen carbonate and an aqueous sodium chloride. The organic layer was dried over sodium sulfate and concentrated to provide a residue, which was chromatographed on silica gel (developing solvent: dichloromethane and diethyl ether, 10:1 v/v) to give 17-allyl-12-[2-[4-[(−)-2-trifluoromethyl-2-methoxy-2-phenylacetoxy]-3-methoxycyclohexyl]-1-methylvinyl]-1,14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone (6.5 mg) and 17-allyl-14-[(−)-2-trifluoromethyl-2-methoxy-2-phenylacetoxy]-12-[2-[4-[(−)-2-trifluoromethyl-3-methoxy-3-phenylacetoxy]-3-methoxycyclohexyl]-1-methylvinyl]-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo-[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone (20.2 mg).

WORKUP

后处理

stirringby stirring at room temperature for 3.5 hours
concentrationThe resulting solution was concentrated
customto provide a residue, which
washwashed successively with hydrochloric acid
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated
customto provide a residue, which
customwas chromatographed on silica gel (developing solvent: dichloromethane and diethyl ether, 10:1 v/v)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-bf4291387a254a9aa2cef4882b51f0f9
来源数据集: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06201005B1
来源说明: uspto-grants-2001_03

反应 SMILES

[F:1][C:2]([F:16])([F:15])[C:3]([O:13][CH3:14])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([OH:6])=[O:5].C1(N=C=NC2CCCCC2)CCCCC1.[CH3:32][C@H:33]1[CH2:64][C:63]([CH3:65])=[CH:62][C@@H:61]([CH2:66][CH:67]=[CH2:68])[C:59](=[O:60])[CH2:58][C@H:57]([OH:69])[C@@H:56]([CH3:70])[C@@H:55](/[C:71](/[CH3:82])=[CH:72]/[C@H:73]2[CH2:78][C@@H:77]([O:79][CH3:80])[C@H:76](O)[CH2:75][CH2:74]2)[O:54][C:52](=[O:53])[C@H:51]2[N:46]([CH2:47][CH2:48][CH2:49][CH2:50]2)[C:44](=[O:45])[C:42](=[O:43])[C@:40]2([OH:83])[O:41][C@@H:36]([C@@H:37]([O:85][CH3:86])[CH2:38][C@H:39]2[CH3:84])[C@@H:35]([O:87][CH3:88])[CH2:34]1>C(OCC)(=O)C.CN(C1C=CN=CC=1)C.C(OCC)C>[CH2:66]([CH:61]1[CH:62]=[C:63]([CH3:65])[CH2:64][CH:33]([CH3:32])[CH2:34][CH:35]([O:87][CH3:88])[CH:36]2[O:41][C:40]([OH:83])([CH:39]([CH3:84])[CH2:38][CH:37]2[O:85][CH3:86])[C:42](=[O:43])[C:44](=[O:45])[N:46]2[CH:51]([CH2:50][CH2:49][CH2:48][CH2:47]2)[C:52](=[O:53])[O:54][CH:55]([C:71]([CH3:82])=[CH:72][CH:73]2[CH2:74][CH2:75][CH:76]([O:5][C:4](=[O:6])[C:3]([C:2]([F:15])([F:16])[F:1])([O:13][CH3:14])[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:77]([O:79][CH3:80])[CH2:78]2)[CH:56]([CH3:70])[CH:57]([OH:69])[CH2:58][C:59]1=[O:60])[CH:67]=[CH2:68]