HRID1923974

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID14798

Sodium Hydroxide

HNaO

结构：COC(=O)[C@H](CCC(=S)N(CCNC(=O)OC(C)(C)C)CCNC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C

HCID59366732

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)NCCN(CCNC(=O)OC(C)(C)C)C(=S)CC[C@H](NC(=O)OC(C)(C)C)C(=O)O

HCID59366983

未命名化合物

收率 88.2%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID887

Methanol

CH4O

PROCEDURE

实验过程

To the solution of the ester XV (290 mg, 0.51 mmol) in MeOH (10 mL) was added 4 M NaOH dropwise until pH=13. The mixture was stirred overnight at r.t. before evaporating the MeOH under reduced pressure. The residue was mixed with water and washed with ether. After acidifying to pH˜3 with 2 M HCl, the product was extracted with DCM, dried over MgSO4 and concentrated under vacuum to give (2S)-4-[bis(2-{[(tert-butoxy)carbonyl]amino}ethyl)carbamothioyl]-2-{[(tert-butoxy)carbonyl]amino}butanoic acid XVI (250 mg, 0.45 mmol, 88% yield). ESIMS found for C24H44N4O8S m/z 549 (M+H).

WORKUP

后处理

custombefore evaporating the MeOH under reduced pressure
additionThe residue was mixed with water
washwashed with ether
extractionthe product was extracted with DCM
dry with materialdried over MgSO4
concentrationconcentrated under vacuum

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-098228d0c9694843b46de188715445b8
来源数据集: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08178490B2
来源说明: uspto-grants-2012_05

反应 SMILES

[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:29][CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:12]([CH2:14][CH2:15][C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:17]([O:19]C)=[O:18])=[S:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:35]([O:34][C:32]([NH:31][CH2:30][CH2:29][N:11]([CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:12]([CH2:14][CH2:15][C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[C:17]([OH:19])=[O:18])=[S:13])=[O:33])([CH3:36])([CH3:37])[CH3:38]