HRID444997

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID81531

Diisopropylethylamine

C8H19N

结构：CN(C)C(ON1C(=O)CCC1=O)=[N+](C)C.F[B-](F)(F)F

HCID9857522

TSTU

C9H16BF4N3O3

结构：CC(C)(C)OC(=O)CCCCCCCCCCCCCCCCC(=O)N(CCC(=O)OC(C)(C)C)CC(=O)Nc1cc(C(=O)O)cc(C(=O)OC(C)(C)C)c1

HCID66724499

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)CCCCCCCCCCCCCCCCC(=O)N(CCC(=O)OC(C)(C)C)CC(=O)Nc1cc(C(=O)ON2C(=O)CCC2=O)cc(C(=O)OC(C)(C)C)c1

HCID87125730

未命名化合物

收率 90%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

5-{2-[(2-tert-Butoxycarbonyl-ethyl)-(17-tert-butoxycarbonyl-heptadecanoyl)-amino]-acetylamino}-isophthalic acid mono-tert-butyl ester (214 mg) was dissolved in dry THF and TSTU (0.105 mg) and DIPEA (0.1 ml) was added. The mixture was stirred at room temperature under nitrogen. After 20 h the reaction mixture was concentrated. The residue was redissolved in EtOAc and filteret. The filtrate was extracted with 0.1 N HCl (2×) and brine (1×), dried (Na2SO4) and concentrated to give 5-{2-[(2-tert-Butoxycarbonyl-ethyl)-(17-tert-butoxycarbonyl-heptadecanoyl)-amino]-acetylamino}-isophthalic acid 1-tert-butyl ester 3-(2,5-dioxo-pyrrolidin-1-yl) ester as a yellow sirup in 90% yield (218 mg).

WORKUP

后处理

concentrationAfter 20 h the reaction mixture was concentrated
dissolutionThe residue was redissolved in EtOAc
extractionThe filtrate was extracted with 0.1 N HCl (2×) and brine (1×)
dry with materialdried (Na2SO4)
concentrationconcentrated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-4595c7462dba4b15aa93ac274035e949
来源数据集: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08476228B2
来源说明: uspto-grants-2013_07

反应 SMILES

[C:1]([O:5][C:6](=[O:55])[C:7]1[CH:15]=[C:14]([NH:16][C:17](=[O:54])[CH2:18][N:19]([CH2:45][CH2:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C:20](=[O:44])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH:13]=[C:9]([C:10]([OH:12])=[O:11])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)F.CN(C(O[N:69]1[C:74](=[O:75])[CH2:73][CH2:72][C:70]1=[O:71])=[N+](C)C)C.CCN(C(C)C)C(C)C>C1COCC1>[O:71]=[C:70]1[CH2:72][CH2:73][C:74](=[O:75])[N:69]1[O:11][C:10](=[O:12])[C:9]1[CH:8]=[C:7]([CH:15]=[C:14]([NH:16][C:17](=[O:54])[CH2:18][N:19]([CH2:45][CH2:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C:20](=[O:44])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:38])[CH:13]=1)[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:55]