HRID64521

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID7515

N-Methylaniline

C7H9N

HCID8857

Ethyl acetate

C4H8O2

HCID516920

Potassium bisulfate

HKO4S

结构：C=CCOC(=O)[C@H](Cc1ccc(OP(=O)(Cc2ccccc2)Cc2ccccc2)c(N=[N+]=[N-])c1)NC(=O)OCC1c2ccccc2-c2ccccc21

HCID86720300

未命名化合物

PRODUCTS

生成物

结构：[N-]=[N+]=Nc1cc(C[C@H](NC(=O)OCC2c3ccccc3-c3ccccc32)C(=O)O)ccc1OP(=O)(Cc1ccccc1)Cc1ccccc1

HCID86720299

未命名化合物

收率 44.1%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

Fmoc-3-azido-O-(dibenzylphosphoryl)tyrosine allyl ester 11 (969 mg, 1.30 mmol) was dissolved in dry THF (10 mL), after which N-methylaniline (0.42 mL, 3.9 mmol) and tetrakis triphenylphosphine palladium (75 mg, 0.065 mmol) were added. After stirring for 2 h at room temperature under a N2-atmosphere in the dark, EtOAc (30 mL) and 1M KHSO4 (30 mL) were added. After drying on Na2SO4 and column chromatography (3% MeOH in DCM), the product (386 mg, 42%) was obtained as a white foam.

WORKUP

后处理

additionwere added
dry with materialAfter drying on Na2SO4 and column chromatography (3% MeOH in DCM)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-2c14008d6ec34614867f44cebe26e520
来源数据集: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09448237B2
来源说明: uspto-grants-2016_09

反应 SMILES

C([O:4][C:5](=[O:52])[C@H:6]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][P:33]([CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:34])=[C:28]([N:49]=[N+:50]=[N-:51])[CH:27]=1)[NH:7][C:8]([O:10][CH2:11][CH:12]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:9])C=C.CNC1C=CC=CC=1.CCOC(C)=O.OS([O-])(=O)=O.[K+]>C1COCC1>[C:8]([NH:7][C@H:6]([C:5]([OH:52])=[O:4])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][P:33]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([CH2:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)=[O:34])=[C:28]([N:49]=[N+:50]=[N-:51])[CH:27]=1)([O:10][CH2:11][CH:12]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:9]