HRID1482073

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID2723923

Formic acid, ammonium salt

CH5NO2

反应SMILES：COC(=O)[C@@H](OC(C)(C)C)c1c(C)c(Br)c2nc3c(Br)n2c1N1CCC(C)(CC1)OCCCC[C@H](C)Oc1c(F)cccc1-c1cccc-3c1

HCID118316318

未命名化合物

PRODUCTS

产物

反应SMILES：COC(=O)[C@@H](OC(C)(C)C)c1c(C)c(Br)c2nc3cn2c1N1CCC(C)(CC1)OCCCC[C@H](C)Oc1c(F)cccc1-c1cccc-3c1

HCID118316321

未命名化合物

收率 59.6%

AUXILIARIES

试剂、催化剂与溶剂

反应SMILES：c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1

催化剂HCID178418397

未命名化合物

溶剂HCID6228

Dimethylformamide

C3H7NO

溶剂HCID8857

Ethyl acetate

C4H8O2

CONDITIONS

反应条件

温度: 40 °C

PROCEDURE

实验过程

Methyl(2S)-2-(tert-butoxy)-2-[(22S)-5,8-dibromo-19-fluoro-4,22,28-trimethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate (0.13 g, 0.16 mmol, 1.0 equiv) and ammonium formate (0.101 g, 1.6 mmol, 10.0 equiv) were dissolved in DMF (3.19 mL). To this solution was added tetrakis (0.018 g, 0.016 mmol, 0.1 equiv). The mixture was heated at 40° C. overnight. Then it was diluted with ethyl acetate, washed by NaHCO3, dried over MgSO4, concentrated and purified by flash column (24 g, 0-100% EtOAc[2% TEA]/Hex) to afford the product (70 mg, 59.6%). LCMS (ESI, M+1): 736.3.

WORKUP

后处理

washwashed by NaHCO3
dry with materialdried over MgSO4
concentrationconcentrated
custompurified by flash column (24 g, 0-100% EtOAc[2% TEA]/Hex)

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-de6299c656ee46d2a243b61573ecb8d8
来源数据集: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US09409922B2
来源说明: uspto-grants-2016_08

反应SMILES

[C:1]([O:5][C@@H:6]([C:11]1[C:40]([CH3:41])=[C:39]([Br:42])[C:38]2=[N:43][C:35]3=[C:36](Br)[N:37]2[C:12]=1[N:13]1[CH2:49][CH2:48][C:16]([CH3:50])([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([CH3:47])[O:23][C:24]2[C:25]([F:46])=[CH:26][CH:27]=[CH:28][C:29]=2[C:30]2[CH:45]=[C:34]3[CH:33]=[CH:32][CH:31]=2)[CH2:15][CH2:14]1)[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CN(C=O)C.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:42][C:39]1[C:38]2=[N:43][C:35]3=[CH:36][N:37]2[C:12]([N:13]2[CH2:14][CH2:15][C:16]([CH3:50])([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([CH3:47])[O:23][C:24]4[C:25]([F:46])=[CH:26][CH:27]=[CH:28][C:29]=4[C:30]4[CH:45]=[C:34]3[CH:33]=[CH:32][CH:31]=4)[CH2:48][CH2:49]2)=[C:11]([C@H:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:7]([O:9][CH3:10])=[O:8])[C:40]=1[CH3:41]