HRID1055442

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID962

Water

H2O

HCID8016

N-Methyl-N-hydroxyethylamine

C3H9NO

HCID75771

1-Hydroxybenzotriazole

C6H5N3O

HCID81531

Diisopropylethylamine

C8H19N

结构：CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[P-](F)(F)(F)(F)F

HCID2733084

Methanaminium, N-[(1H-benzotriazol-1-yloxy)(dimethylamino)methylene]-N-methyl-, hexafluorophosphate(1-) (1:1)

C11H16F6N5OP

结构：COc1ccc2cc(C(=O)O)ccc2c1CN1C(=O)[C@@H](NC(=O)[C@H](C)N(C)C(=O)OC(C)(C)C)COc2ccccc21

HCID118574193

未命名化合物

PRODUCTS

生成物

结构：COc1ccc2cc(C(=O)N(C)CCO)ccc2c1CN1C(=O)[C@@H](NC(=O)[C@H](C)N(C)C(=O)OC(C)(C)C)COc2ccccc21

HCID131736359

未命名化合物

收率 85.6%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

A mixture of 5-(((S)-3-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-4-oxo-3,4-dihydrobenzo[b][1,4]oxazepin-5(2H)-yl)methyl)-6-methoxy-2-naphthoic acid (100 mg, 173 μmol, Eq: 1.00), 2-(methylamino)ethanol (26.0 mg, 27.8 μl, 346 μmol, Eq: 2.00), HOBT.H2O (31.8 mg, 208 μmol, Eq: 1.20), HBTU (78.8 mg, 208 μmol, Eq: 1.2), DIEA (67.1 mg, 90.5 μl, 519 μmol, Eq: 3.00) in DMF was stirred at 0° C. for 2 h. The mixture was diluted with EtOAc, washed with water, brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography to afford tert-butyl (S)-1-((S)-5-((6-((2-hydroxyethyl)(methyl)carbamoyl)-2-methoxynaphthalen-1-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (94 mg, 85% yield) as an oil.

WORKUP

后处理

washwashed with water, brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe residue was purified by silica gel chromatography

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-df8b2e2309c54d5ba96ba39eaa94fcb4
来源数据集: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09394263B2
来源说明: uspto-grants-2016_07

反应 SMILES

[C:1]([O:5][C:6]([N:8]([CH3:42])[C@@H:9]([CH3:41])[C:10]([NH:12][C@H:13]1[CH2:19][O:18][C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[N:15]([CH2:24][C:25]2[C:34]([O:35][CH3:36])=[CH:33][CH:32]=[C:31]3[C:26]=2[CH:27]=[CH:28][C:29]([C:37]([OH:39])=O)=[CH:30]3)[C:14]1=[O:40])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:43][NH:44][CH2:45][CH2:46][OH:47].C1C=CC2N(O)N=NC=2C=1.O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[OH:47][CH2:46][CH2:45][N:44]([CH3:43])[C:37]([C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][CH:28]=1)[C:25]([CH2:24][N:15]1[C:14](=[O:40])[C@@H:13]([NH:12][C:10](=[O:11])[C@@H:9]([N:8]([CH3:42])[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH3:41])[CH2:19][O:18][C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]1=3)=[C:34]([O:35][CH3:36])[CH:33]=[CH:32]2)=[O:39]