HRID1433297

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID222

Ammonia gas

H3N

HCID887

Methanol

CH4O

HCID175505

Triethylamine trihydrofluoride

C6H18F3N

结构：CC(C)N(CC[C@H](c1ccccc1)c1cc(OCCCCCCCNC[C@H](O[Si](C)(C)C(C)(C)C)c2ccc(O)c(NS(C)(=O)=O)c2)ccc1O)C(C)C

HCID57933236

未命名化合物

PRODUCTS

生成物

HCID222

Ammonia gas

H3N

结构：CC(C)N(CC[C@H](c1ccccc1)c1cc(OCCCCCCCNC[C@H](O)c2ccc(O)c(NS(C)(=O)=O)c2)ccc1O)C(C)C

HCID57933206

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

N-(5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[(7-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenoxy}heptyl)amino]ethyl}-2-hydroxyphenyl)methanesulfonamide (Preparation 20, 68 mg, 0.087 mmol) was dissolved in tetrahydrofuran (3 ml) and N,N-diethylethanamine trihydrofluoride (71 μl, 0.43 mmol) was added dropwise. After 18 hours a mixture of methanol (4 ml) and 880 ammonia (8 ml) were added and after 15 minutes the solvent was removed in vacuo. The residue was dissolved in dichloromethane and the solvent removed in vacuo again and the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (97/310.3 to 88/12/1.2 by volume) to furnish the title compound as a white solid, 30 mg.

WORKUP

后处理

additionwere added and after 15 minutes the solvent
customwas removed in vacuo
dissolutionThe residue was dissolved in dichloromethane
customthe solvent removed in vacuo again
customthe residue was purified by column chromatography on silica gel eluting with dichloromethane

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-5e60114b731441e7837b3e6e48e39fd4
来源数据集: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07612084B2
来源说明: uspto-grants-2009_11

反应 SMILES

[Si]([O:8][C@H:9]([C:43]1[CH:44]=[CH:45][C:46]([OH:54])=[C:47]([NH:49][S:50]([CH3:53])(=[O:52])=[O:51])[CH:48]=1)[CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([C@@H:27]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:28][CH2:29][N:30]([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32])[CH:21]=1)(C(C)(C)C)(C)C.F.F.F.C(N(CC)CC)C.CO.N>O1CCCC1>[NH3:11].[CH:34]([N:30]([CH:31]([CH3:33])[CH3:32])[CH2:29][CH2:28][C@@H:27]([C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[OH:26])[O:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]([C:43]1[CH:44]=[CH:45][C:46]([OH:54])=[C:47]([NH:49][S:50]([CH3:53])(=[O:52])=[O:51])[CH:48]=1)[OH:8])[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)([CH3:36])[CH3:35]