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HRID1666533

反应详情

EQUATION

反应方程式

HRID 1666533 的结构方程式

REACTANTS

反应物

2
结构：O.[Li+].[OH-]
HCID168937

Lithium hydroxide, monohydrate

H3LiO2

3 次

结构：CCCCS[C@@]1(c2ccc(-c3ccccc3)cc2)C[C@H]2C(=O)N[C@]3(C(=O)OCC)C[C@H]3/C=C\CCCCC[C@H](NC(=O)OC(C)(C)C)C(=O)N2C1
HCID57988332

未命名化合物

PRODUCTS

生成物

1
结构：CCCCS[C@@]1(c2ccc(-c3ccccc3)cc2)C[C@H]2C(=O)N[C@]3(C(=O)O)C[C@H]3/C=C\CCCCC[C@H](NC(=O)OC(C)(C)C)C(=O)N2C1
HCID57988333

未命名化合物

收率 90.2%

AUXILIARIES

试剂、催化剂与溶剂

3
结构：CO
溶剂HCID887

Methanol

CH4O

结构：O
溶剂HCID962

Water

H2O

3 次

结构：C1CCOC1
溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

To a solution of (2R,6S,13aS,14aR,16aS,Z)-ethyl 2-(biphenyl-4-yl)-6-(tert-butoxycarbonylamino)-2-(butylthio)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (59 mg, 0.082 mmol) in THF (1 mL) and MeOH (1.000 mL) was added pre-made solution of Lithium hydroxide monohydrate (6.90 mg, 0.164 mmol) in water (1 mL). The resulting cloudy solution was stirred at room for 5 h. LC/MS analysis showed partial reaction. Another portion of Lithium hydroxide monohydrate (6.90 mg, 0.164 mmol) in water (0.2 ml) was added and stirred for additional 17 hours. LC/MS analysis showed there was still small portion of starting material remained. Another portion of Lithium hydroxide monohydrate (6.90 mg, 0.164 mmol) in water (0.2 ml) was added and stirred for additional 5 hours. Quenched with 5% citric acid, extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated to afford the desired product (2R,6S,13aS,14aR,16aS,Z)-2-(biphenyl-4-yl)-6-(tert-butoxycarbonylamino)-2-(butylthio)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylic acid (57 mg, 0.074 mmol, 90% yield) as a white foam. 1H NMR (500 MHz, MeOD) δ ppm 0.84 (t, J=7.32 Hz, 3 H) 1.14-1.37 (m, 5 H) 1.38-1.54 (m, 16 H) 1.53-1.68 (m, 4 H) 1.82-1.95 (m, 1 H) 1.96-2.12 (m, 1 H) 2.21-2.38 (m, 2 H) 2.42 (dt, J=12.21, 7.17 Hz, 1 H) 2.48-2.63 (m, 1 H) 2.84-3.00 (m, 1 H) 3.92-4.18 (m, 2 H) 4.49 (dd, J=10.38, 2.75 Hz, 1 H) 5.18 (d, J=10.68 Hz, 1 H) 5.35 (t, J=9.77 Hz, 1 H) 5.56-5.68 (m, 1 H) 7.30-7.39 (m, 1 H) 7.45 (t, J=7.63 Hz, 2 H) 7.55-7.63 (m, 4 H) 7.77 (d, J=8.24 Hz, 2 H). LC-MS (retention time: 3.34 min, method C), MS m/z 690(M+H).

WORKUP

后处理

  1. customreaction
  2. stirringstirred for additional 17 hours
  3. stirringstirred for additional 5 hours
  4. customQuenched with 5% citric acid
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated