HRID2250810

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID81531

Diisopropylethylamine

C8H19N

反应SMILES：CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F

HCID9886157

Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

C10H15F6N6OP

反应SMILES：CC(C)(C)OC(=O)Nc1cc(NC(=O)CC(=O)O)cc(C(F)(F)F)c1

HCID21111788

未命名化合物

反应SMILES：CC#C[C@H](O)[C@@H](N)CNC(=O)OCc1ccccc1

HCID69196343

未命名化合物

PRODUCTS

产物

反应SMILES：CC#C[C@H](O)[C@H](CNC(=O)OCc1ccccc1)NC(=O)CC(=O)Nc1cc(NC(=O)OC(C)(C)C)cc(C(F)(F)F)c1

HCID86596719

未命名化合物

收率 23.4%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID22350042

未命名化合物

PROCEDURE

实验过程

A solution of (2S, 3S)-(2-amino-3-hydroxy-hex-4-ynyl)-carbamic acid benzyl ester (225 mg, prepared as in WO PCT 0250019) in 3:1 CH2Cl2/DMF (12 mL) was charged successively with N,N-diisopropylethylamine (0.54 mL), 3-(3-(tert-butoxycarbonyl)amino-5-(trifluoromethyl)phenylamino)-3-oxopropanoic acid 235 mg), and HATU (283 mg). The reaction was stirred for 14 h at RT before being partitioned between EtOAc and water. The organic phase was washed with sat. NH4Cl, water, and brine before being dried (Na2SO4), filtered, and concentrated in vacuo. Flash chromatography provided benzyl (2S,3S)-2-(3-(3-(tert-butoxycarbonyl)amino-5-(trifluoromethyl)phenylamino)-3-oxopropanamido)-3-hydroxyhex-4-ynylcarbamate (92 mg). MS found: (M+Na)+=629.4.

WORKUP

后处理

custombefore being partitioned between EtOAc and water
washThe organic phase was washed with sat. NH4Cl, water, and brine
dry with materialbefore being dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-42c340ef7a614574aed9f0023aa003f2
来源数据集: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US07317019B2
来源说明: uspto-grants-2008_01

反应SMILES

[CH2:1]([O:8][C:9](=[O:19])[NH:10][CH2:11][C@H:12]([NH2:18])[C@@H:13]([OH:17])[C:14]#[C:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[C:29]([O:33][C:34]([NH:36][C:37]1[CH:38]=[C:39]([NH:47][C:48](=[O:53])[CH2:49][C:50](O)=[O:51])[CH:40]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:42]=1)=[O:35])([CH3:32])([CH3:31])[CH3:30].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.CN(C=O)C>[C:29]([O:33][C:34]([NH:36][C:37]1[CH:38]=[C:39]([NH:47][C:48](=[O:53])[CH2:49][C:50]([NH:18][C@H:12]([C@@H:13]([OH:17])[C:14]#[C:15][CH3:16])[CH2:11][NH:10][C:9](=[O:19])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:51])[CH:40]=[C:41]([C:43]([F:44])([F:45])[F:46])[CH:42]=1)=[O:35])([CH3:32])([CH3:30])[CH3:31]