HRID1486108

反应详情

EQUATION

反应方程式

REACTANTS

反应物

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

HCID7009590

未命名化合物

结构：COc1ccc2ccccc2c1CN1C(=O)[C@@H](N)[C@H](C)N(C(C)=O)c2cc(C#N)ccc21.Cl

HCID72712573

未命名化合物

PRODUCTS

生成物

结构：COc1ccc2ccccc2c1CN1C(=O)[C@@H](NC(=O)[C@H](C)N(C)C(=O)OC(C)(C)C)[C@H](C)N(C(C)=O)c2cc(C#N)ccc21

HCID72712575

未命名化合物

收率 89.4%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

To a 0° C. solution of (3S,4S)-5-acetyl-3-amino-1-((2-methoxynaphthalen-1-yl)methyl)-4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbonitrile hydrochloride (216 mg, 465 μmol) in DMF (1.55 ml) was added Boc-N-methyl-L-alanine (104 mg, 511 μmol), N,N-diisopropylethylamine (322 μl, 1.86 mmol), and HBTU (194 mg, 511 μmol). The reaction was stirred at rt for 30 min, then diluted with H2O and the solids were collected by vacuum filtration, taken up in EtOAc, washed with H2O, sat. aq. NaHCO3, and sat. aq. NaCl, dried over Na2SO4, filtered, and concentrated. The crude material was purified by flash chromatography to provide tert-butyl(S)-1-((3S,4S)-5-acetyl-7-cyano-1-((2-methoxynaphthalen-1-yl)methyl)-4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (255 mg, 89%) as a white solid. MS m/z 636 (MNa)+.

WORKUP

后处理

filtrationthe solids were collected by vacuum filtration
washwashed with H2O, sat. aq. NaHCO3, and sat. aq. NaCl
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude material was purified by flash chromatography

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-a1debe133d684275bea6c82a8d0988c7
来源数据集: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09422331B2
来源说明: uspto-grants-2016_08

反应 SMILES

Cl.[C:2]([N:5]1[C@@H:11]([CH3:12])[C@H:10]([NH2:13])[C:9](=[O:14])[N:8]([CH2:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][C:17]=2[O:26][CH3:27])[C:7]2[CH:28]=[CH:29][C:30]([C:32]#[N:33])=[CH:31][C:6]1=2)(=[O:4])[CH3:3].[C:34]([N:41]([CH3:47])[C@H:42]([C:44](O)=[O:45])[CH3:43])([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[C:2]([N:5]1[C@@H:11]([CH3:12])[C@H:10]([NH:13][C:44](=[O:45])[C@@H:42]([N:41]([CH3:47])[C:34](=[O:35])[O:36][C:37]([CH3:38])([CH3:40])[CH3:39])[CH3:43])[C:9](=[O:14])[N:8]([CH2:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][C:17]=2[O:26][CH3:27])[C:7]2[CH:28]=[CH:29][C:30]([C:32]#[N:33])=[CH:31][C:6]1=2)(=[O:4])[CH3:3]