HRID376559

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID1049

Pyridine

C5H5N

HCID31297

Methanesulfonyl chloride

CH3ClO2S

HCID81531

Diisopropylethylamine

C8H19N

$结构：CO/N=C(\C(=O)O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1.Cl$

HCID9566066

未命名化合物

结构：CC(C)(C)OC(=O)C1=C(C2CCCO2)CS[C@@H]2[C@H](N)C(=O)N12

HCID54097811

未命名化合物

PRODUCTS

生成物

$结构：CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)OC(C)(C)C)=C(C3CCCO3)CS[C@H]12)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1$

HCID141582269

未命名化合物

收率 84%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

2 次

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

Mesyl chloride (141μl, 1.8mmol) was added to 2-(Z)-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetic acid hydrochloride (0.744g, 1.65mmol) and N,N-diisopropylethylamine (576μl, 3.3mmol) in DMF (5ml) at -40° C. The reaction mixture was stirred 0.5h at -30±10° C. then t-butyl (6R,7R)-7-amino-3-(tetrahydrofuran-2-yl)ceph-3-em-4-carboxylate, more mobile diastereoisomer (0.431g, 1.3mmol) in DMF (5ml) followed by pyridine (1471μl, 1.8mmol) were added. Stirred 1h without further cooling then diluted with ethyl acetate, washed twice with water and with brine, dried, concentrated and flash chromatographed on silica gel eluting with 30,35 and 40% ethyl acetate in hexane to give the title compound as a foam (0.83g, 84%); vmax (CH2Cl2) 3396, 3277, 1782, 1732, 1683, 1526, 1248, 1156 and 1051cm-1 ; δH [(CD3)2SO, 250MHz]1.47 (9H, s), 1.55-1.75 (1H, m), 1.8-2.0 (2H, m), 2.05-2.2 (1H, m), 3.44 and 3.50 (2H, ABq, J18.3Hz), 3.65-3.95 (2H, m), 3.81 (3H, s), 4.6-4.7 (1H, m), 5.14 (1H, d, J4.8Hz), 5.66 (1H, dd, J4.8, 7.9Hz), 6.70 (1H, s), 7.2-7.4 (15H, m), 8.88 (1H, s) and 9.54 (1H, d, J7.9Hz). [Mass spectrum: +ve ion (3-nitrobenzyl alcohol, sodium acetate) MNa+ (774)].

WORKUP

后处理

additionwere added
temperaturewithout further cooling
washwashed twice with water and with brine
customdried
concentrationconcentrated
customflash chromatographed on silica gel eluting with 30,35 and 40% ethyl acetate in hexane

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-aa3496bd25d646e2b394919c7c0d6492
来源数据集: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06020329
来源说明: uspto-grants-2000_02

反应 SMILES

S(Cl)(C)(=O)=O.Cl.[CH3:7][O:8]/[N:9]=[C:10](/[C:14]1[N:15]=[C:16]([NH:19][C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:17][CH:18]=1)\[C:11](O)=[O:12].C(N(CC)C(C)C)(C)C.[NH2:48][C@@H:49]1[C:68](=[O:69])[N:51]2[C:52]([C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])=[C:53]([CH:56]3[CH2:60][CH2:59][CH2:58][O:57]3)[CH2:54][S:55][C@H:50]12.N1C=CC=CC=1>CN(C=O)C.C(OCC)(=O)C>[CH3:7][O:8]/[N:9]=[C:10](/[C:14]1[N:15]=[C:16]([NH:19][C:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[S:17][CH:18]=1)\[C:11]([NH:48][C@@H:49]1[C:68](=[O:69])[N:51]2[C:52]([C:61]([O:63][C:64]([CH3:65])([CH3:67])[CH3:66])=[O:62])=[C:53]([CH:56]3[CH2:60][CH2:59][CH2:58][O:57]3)[CH2:54][S:55][C@H:50]12)=[O:12]