HRID26333

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID313

Hydrochloric Acid

ClH

HCID3283

Diethyl Ether

C4H10O

结构：CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)ON1C(=O)CCC1=O

HCID98768

tert-Butyl (S)-(1-(((2,5-dioxopyrrolidin-1-yl)oxy)carbonyl)-2-methylpropyl)carbamate

C14H22N2O6

结构：C[C@@H](OCc1ccccc1)[C@H](NC(=O)[C@@H](N)CC(=O)OCc1ccccc1)C(=O)N[C@@H](COCc1ccccc1)C(=O)N[C@@H](COCc1ccccc1)C(=O)N[C@@H](CCC(=O)OCc1ccccc1)C(=O)O

HCID131711281

未命名化合物

PRODUCTS

生成物

结构：CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@@H](CC(=O)OCc1ccccc1)C(=O)N[C@H](C(=O)N[C@@H](COCc1ccccc1)C(=O)N[C@@H](COCc1ccccc1)C(=O)N[C@@H](CCC(=O)OCc1ccccc1)C(=O)O)[C@@H](C)OCc1ccccc1

HCID131711280

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

溶剂HCID8028

Tetrahydrofuran

C4H8O

2 次

溶剂HCID8471

Triethylamine

C6H15N

2 次

PROCEDURE

实验过程

Boc-Asp(OBzl)-Thr(Bzl)-Ser(Bzl)-Ser(Bzl)-Glu(OBzl)-OH (50.0 g, 46 mmol) was deprotected with HCl (4.15 N) in THF and worked up as usual to give 45.4 g of white solid. It was dissolved in THF (1.5 liters) and treated with ether (7 liters). On standing at 0° overnight a white solid powder was obtained (44.0 g, mp 179°-184°). Part of this material, HCl.H-Asp(OBzl)-Thr(Bzl)-Ser(Bzl)-Ser(Bzl)-Glu(OBzl)-OH (43.7 g, 42.7 mmol) was then dissolved in 500 ml of DMF, cooled to 0°, and treated with Boc-Val-OSu (15.4 g, 49 mmol) and Et3N (10 ml). The mixture was stirred for 15 hours during which time more Et3N (7.9 ml) was added in several portions maintaining the reaction slightly basic. The insoluble matter was removed by filtration and the filtrate evaporated to dryness. The oily residue was dissolved in CH2Cl2, washed with 5% HOAc, H2O, dried (Na2SO4), and evaporated to a smaller volume (0.5 liter) when treated with petroleum ether. The product crystallized slowly during overnight standing. It was recrystallized from THF and i-PrOH to yield, 26.3 g (51.4%); mp 174°-177°; α]D25 =+0.84° (c, 1, THF).

WORKUP

后处理

customa white solid powder was obtained (44.0 g, mp 179°-184°)
temperaturecooled to 0°
additionwas added in several portions
temperaturemaintaining
customthe reaction slightly basic
customThe insoluble matter was removed by filtration
customthe filtrate evaporated to dryness
dissolutionThe oily residue was dissolved in CH2Cl2
washwashed with 5% HOAc, H2O
dry with materialdried (Na2SO4)
customevaporated to a smaller volume (0.5 liter) when
additiontreated with petroleum ether
customThe product crystallized slowly during overnight
customIt was recrystallized from THF and i-PrOH
customto yield

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-101eefa9a8d24c31a3ac4402adca4457
来源数据集: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04148788
来源说明: uspto-grants-1979_04

反应 SMILES

CCOCC.Cl.[NH2:7][C@H:8]([C:20]([NH:22][C@H:23]([C:34]([NH:36][C@H:37]([C:47]([NH:49][C@H:50]([C:60]([NH:62][C@H:63]([C:76]([OH:78])=[O:77])[CH2:64][CH2:65][C:66](=[O:75])[O:67][CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)=[O:61])[CH2:51][O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:48])[CH2:38][O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:35])[C@@H:24]([CH3:33])[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:21])[CH2:9][C:10](=[O:19])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH:79]([C:94]([O:96][C:97]([CH3:100])([CH3:99])[CH3:98])=[O:95])[C@H:80]([C:84](ON1C(=O)CCC1=O)=[O:85])[CH:81]([CH3:83])[CH3:82]>C1COCC1.CN(C=O)C.CCN(CC)CC>[NH:79]([C:94]([O:96][C:97]([CH3:99])([CH3:98])[CH3:100])=[O:95])[C@H:80]([C:84]([NH:7][C@H:8]([C:20]([NH:22][C@H:23]([C:34]([NH:36][C@H:37]([C:47]([NH:49][C@H:50]([C:60]([NH:62][C@H:63]([C:76]([OH:78])=[O:77])[CH2:64][CH2:65][C:66](=[O:75])[O:67][CH2:68][C:69]1[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=1)=[O:61])[CH2:51][O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:48])[CH2:38][O:39][CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)=[O:35])[C@@H:24]([CH3:33])[O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:21])[CH2:9][C:10](=[O:19])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:85])[CH:81]([CH3:82])[CH3:83]