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HRID2273336

反应详情

EQUATION

反应方程式

HRID 2273336 的结构方程式

REACTANTS

反应物

4
结构：ClCCl
HCID6344

Dichloromethane

CH2Cl2

2 次

结构：CC(C)N=C=NC(C)C
HCID12734

Diisopropylcarbodiimide

C7H14N2

结构：CC(C)(C)OC[C@H](NC(=O)OCc1cccc2c1Cc1ccccc1-2)C(=O)O
HCID57046908

未命名化合物

结构：CCCCCCCCCCCCCCO[C@@H]1[C@@H](OCCCCCCCCCCCCCC)[C@@H](OC)O[C@H](COC(=O)CCC(=O)O)[C@H]1OCc1ccc(OC)cc1
HCID89999082

未命名化合物

PRODUCTS

生成物

1
结构：CCCCCCCCCCCCCCO[C@H]1[C@@H](OC)O[C@H](COC(=O)CCC(=O)OC[C@H](NC(=O)OCC2c3ccccc3-c3ccccc32)C(=O)OC(C)(C)C)[C@@H](O)[C@@H]1OCCCCCCCCCCCCCC
HCID89998812

未命名化合物

收率 79%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CN(C)c1ccncc1
催化剂HCID14284

N,N-Dimethylpyridin-4-amine

C7H10N2

PROCEDURE

实验过程

DMAP (6.2 mg, 0.05 mmol) and DIC (0.16 mL, 1.01 mmol) were added to a stirred solution of O-tert-butyl-N-fluorenylmethoxycarbonyl-L-serine 9 (0.39 g, 0.60 mmol) in CH2Cl2 (3 ml). After 1 h, the carboxylic acid derivative 22 (0.41 g, 0.50 mmol) was added and the reaction was stirred for 5-9 h until no further conversion of the starting material could be detected by TLC analysis. The reaction mixture was diluted with CH2Cl2 (20 mL), washed with water (2×10 mL) and brine (10 mL). The organic phase was separated, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate-hexane gradient elution) to afford the title compound 23 (0.47 g, 0.40 mmol) as a colorless amorphous solid in 79% yield. Analytical data for 23: Rf=0.43 (ethyl acetate/hexane, 3/7, v/v); [α]D24+36.1° (c=1.0, CHCl3); 1H NMR (300 MHz, CDCl3): δ, 0.88 (t, 6H, 2×CH3), 1.17 (m, 40H, 20×CH2), 1.38 (s, 9H, t-Bu), 1.54 (m, 4H, 2×CH2), 2.53 (m, 4H, 2×CH2), 3.18 (dd, 1H, J2,3=9.7 Hz, H-2), 3.26 (s, 3H, OCH3), 3.28 (m, 1H, H-4), 3.42-3.66 (m, 5H, H-3, 5, OCH2, OCH2a), 3.67 (s, 3H, OCH3), 3.79 (m, 1H, OCH2b), 4.11-4.46 (m, 8H, H-6a, 6b, ½CH2Ph, Ser-CαH, Ser-CβH2, CH2Fmoc), 4.66 (d, 1H, J1,2=3.3 Hz, H-1), 4.71 (d, 1H, J2=10.5 Hz, ½CH2Ph), 5.71 (d, 1H, JNH,CH=8.1 Hz, Ser-NH), 6.75-7.64 (m, 12H, aromatic) ppm; 13C NMR (75 MHz, CDCl3): δ, 14.2, 22.8, 26.1, 26.4, 28.0, 28.9, 29.5, 29.6, 29.7, 29.8, 30.2, 30.7, 32.0, 47.0, 54.0, 55.2, 55.3, 64.7, 67.3, 68.6, 71.8, 73.8, 74.6, 80.8, 81.8, 83.0, 97.9, 99.7, 113.9, 120.1, 125.2, 125.3, 127.2, 127.8, 129.9, 130.3, 141.4, 142.5, 143.9, 155.9, 159.4, 168.4, 171.7, 172.0, 181.3 ppm; HR FAB MS [M+Na]+ calcd for C69H105NO14Na 1194.7433. found 1194.7433.

WORKUP

后处理

  1. washwashed with water (2×10 mL) and brine (10 mL)
  2. customThe organic phase was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate-hexane gradient elution)