HRID1171958

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID3283

Diethyl Ether

C4H10O

HCID14798

Sodium Hydroxide

HNaO

$结构：CCOC(=O)[C@@]12C[C@H]1/C=C\CCOCC[C@H](NC(=O)OC(C)(C)C)C(=O)N1C[C@H](OC(=O)N3Cc4cccc(F)c4C3)C[C@H]1C(=O)N2$

HCID68787314

未命名化合物

PRODUCTS

生成物

$结构：CC(C)(C)OC(=O)N[C@H]1CCOCC/C=C\[C@@H]2C[C@@]2(C(=O)O)NC(=O)[C@@H]2C[C@@H](OC(=O)N3Cc4cccc(F)c4C3)CN2C1=O$

HCID68787335

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

2 次

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

(2R,6S,13aS,14aR,16aS,Z)-ethyl 6-(tert-butoxycarbonylamino)-2-(4-fluoroisoindoline-2-carbonyloxy)-5,16-dioxo-2,3,5,6,7,8,10,11,13a,14,14a,15,16,16a-tetradecahydro-1H-cyclopropa(j)pyrrolo[1,2-f][1,6,9]oxadiazacyclopentadecine-14a-carboxylate (0.093 g, 0.14 mmol) in THF (2 mL) was added 0.1 N NaOH solution (3.53 ml, 0.35 mmol) in H2O. The reaction was stirred at rt for 3 days. Water (5 mL) and ether (15 mL) was added. The aqueous layer was separated and acidified by saturated potassium hydrogen sulfate solution to pH=2˜3. The aqueous layer was extracted with EA (2×15 mL), washed with brine and dried over sodium sulfate. After removal of solvent, it (2R,6S,13aS,14aR,16aS,Z)-6-(tert-butoxycarbonylamino)-2-(4-fluoroisoindoline-2-carbonyloxy)-5,16-dioxo-2,3,5,6,7,8,10,11,13a,14,14a,15,16,16a-tetradecahydro-1H-cyclopropa(j)pyrrolo[1,2-f][1,6,9]oxadiazacyclopentadecine-14a-carboxylic acid as white solid (0.074 g, 83%). MS: Calcd.: 630; Found: [M+H]+ 631. 1H NMR (400 MHz, d6-DMSO) δ12.25 (s, 1H), 8.77 (s, 1H), 7.37 (m, 1H), 7.07-7.21 (m, 3H), 5.34-5.44 (m, 2H), 5.29 (s, 1H), 4.67 (s, 4H), 4.44 (m, 1H), 4.20 (m, 1H), 3.95 (m, 1H), 3.68 (m, 1H), 3.50 (m, 1H), 3.43 (m, 2H), 3.32 (m, 1H), 2.39 (m, 1H), 2.33 (m, 2H), 2.16 (m, 2H), 1.85 (m, 1H), 1.74 (m, 1H), 1.53 (m, 1H), 1.50 (m, 1H), 1.23 & 0.96 (s, 9H).

WORKUP

后处理

customThe aqueous layer was separated
extractionThe aqueous layer was extracted with EA (2×15 mL)
washwashed with brine
dry with materialdried over sodium sulfate
customAfter removal of solvent, it (2R,6S,13aS,14aR,16aS,Z)-6-(tert-butoxycarbonylamino)-2-(4-fluoroisoindoline-2-carbonyloxy)-5,16-dioxo-2,3,5,6,7,8,10,11,13a,14,14a,15,16,16a-tetradecahydro-1H-cyclopropa(j)pyrrolo[1,2-f][1,6,9]oxadiazacyclopentadecine-14a-carboxylic acid as white solid (0.074 g, 83%)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-2743737970524005873a9e0f4efcc938
来源数据集: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07829665B2
来源说明: uspto-grants-2010_11

反应 SMILES

[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:23](=[O:24])[N:22]2[CH2:25][C@H:26]([O:28][C:29]([N:31]3[CH2:39][C:38]4[C:33](=[CH:34][CH:35]=[CH:36][C:37]=4[F:40])[CH2:32]3)=[O:30])[CH2:27][C@H:21]2[C:20](=[O:41])[NH:19][C@:18]2([C:43]([O:45]CC)=[O:44])[CH2:42][C@H:17]2[CH:16]=[CH:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].CCOCC>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:23](=[O:24])[N:22]2[CH2:25][C@H:26]([O:28][C:29]([N:31]3[CH2:39][C:38]4[C:33](=[CH:34][CH:35]=[CH:36][C:37]=4[F:40])[CH2:32]3)=[O:30])[CH2:27][C@H:21]2[C:20](=[O:41])[NH:19][C@:18]2([C:43]([OH:45])=[O:44])[CH2:42][C@H:17]2[CH:16]=[CH:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]