HRID1732524

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID75771

1-Hydroxybenzotriazole

C6H5N3O

HCID81531

Diisopropylethylamine

C8H19N

结构：CC(C)(C)OC(=O)N[C@@H](CCC(N)=O)C(=O)Oc1ccc([N+](=O)[O-])cc1

HCID7017891

L-Glutamine, N2-[(1,1-dimethylethoxy)carbonyl]-, 4-nitrophenyl ester

C16H21N3O7

结构：CSCC[C@H](NC(=O)[C@H](CCC(N)=O)NC(=O)OC(C)(C)C)C(=O)O

HCID12968638

未命名化合物

结构：CSCC[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)C(C)C

HCID86737377

未命名化合物

PRODUCTS

生成物

结构：CSCC[C@H](NC(=O)[C@H](CCC(N)=O)NC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)C(C)C

HCID86737376

未命名化合物

PROCEDURE

实验过程

The Boc group was removed from a sample of compound XXII (2.5 g, 3.3 mmole) as described in previous paragraphs. The trifluoroacetate salt washed with ether and dried; the white solid (RfC, 0.76) showed on tlc a slight impurity at the origin (presumably the t-butylsulfonium salt). This material was acylated with Boc-L-Gln-ONp (1.4 g, 3.8 mmole, Bachem) in the presence of DIEA (1.3 ml, 8 mmole) and HOBt (0.58 ml, 3.8 mmole). Next day the product was isolated as described for XII and then purified by precipitation from a solution in DMF with H2O. The product was washed with H2O and dried: 28 g (93%), m.p. 238°-241° C. [α]D23 -27.7° (c 0.8, DMF); RfK, 0.43; RfL, 0.50.

WORKUP

后处理

washThe trifluoroacetate salt washed with ether
customdried
customNext day the product was isolated
custompurified by precipitation from a solution in DMF with H2O
washThe product was washed with H2O
customdried

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-0c235137c4a7476f97e5799982b8dd50
来源数据集: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04237046
来源说明: uspto-grants-1980_12

反应 SMILES

[CH2:1]([O:8][C:9](=[O:54])[C@H:10]([CH2:39][CH2:40][CH2:41][CH2:42][NH:43][C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[NH:11][C:12](=[O:38])[C@H:13]([CH:35]([CH3:37])[CH3:36])[NH:14][C:15](=[O:34])[C@H:16]([CH3:33])[NH:17][C:18](=[O:32])[C@H:19]([CH2:28][CH2:29][S:30][CH3:31])[NH:20][C:21](OC(C)(C)C)=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:55]([C:74]([O:76][C:77]([CH3:80])([CH3:79])[CH3:78])=[O:75])[C@H:56](C(OC1C=CC([N+]([O-])=O)=CC=1)=O)[CH2:57][CH2:58][C:59](=[O:61])[NH2:60].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.C(OC(N[C@H](C(N[C@H](C(O)=O)CCSC)=O)CCC(=O)N)=O)(C)(C)C>>[CH2:1]([O:8][C:9](=[O:54])[C@H:10]([CH2:39][CH2:40][CH2:41][CH2:42][NH:43][C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[NH:11][C:12](=[O:38])[C@H:13]([CH:35]([CH3:36])[CH3:37])[NH:14][C:15](=[O:34])[C@H:16]([CH3:33])[NH:17][C:18](=[O:32])[C@H:19]([CH2:28][CH2:29][S:30][CH3:31])[NH:20][C:21](=[O:22])[C@H:56]([CH2:57][CH2:58][C:59](=[O:61])[NH2:60])[NH:55][C:74]([O:76][C:77]([CH3:80])([CH3:78])[CH3:79])=[O:75])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1