Chlorosuccinimide → HCID 15218404, compound

HRID 1456849Notes

Reaction equation

HRID 1456849 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][CH:10]([CH3:40])[C:11]([O:13][C@@H:14]1[C@@H:18]([CH2:19][O:20][C:21](=[O:25])[CH:22]([CH3:24])[CH3:23])[O:17][C@@H:16]([N:26]2[C:30]3[N:31]=[C:32]([NH:37][CH:38]=[O:39])[N:33]=[C:34]([O:35][CH3:36])[C:29]=3[CH:28]=[CH:27]2)[CH2:15]1)=[O:12]>C(Cl)Cl>[Cl:1][C:28]1[C:29]2[C:34]([O:35][CH3:36])=[N:33][C:32]([NH:37][CH:38]=[O:39])=[N:31][C:30]=2[N:26]([C@@H:16]2[O:17][C@H:18]([CH2:19][O:20][C:21](=[O:25])[CH:22]([CH3:23])[CH3:24])[C@@H:14]([O:13][C:11](=[O:12])[CH:10]([CH3:40])[CH3:9])[CH2:15]2)[CH:27]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 11113110HCID 11113110, compound

Product 1

HCID 15218404HCID 15218404, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Chlorosuccinimide (87 mg, 0.67 mmol) is added to a solution of compound (18) (300 mg, 0.67 mmol in 5 ml of DMF). After it has been stirred (at room temperature for 20 h), the solution is added to a mixture of CH2Cl2 /5% aq. NaHCO3 (50 ml, 9:1). The organic layer is separated off, washed with water, dried over Na2SO4, filtered and evaporated. The evaporated residue is dissolved in CH2Cl2 and this solution is chromatographed on silica gel (column: 5×20 cm, CH2Cl2 /acetone, 95:5). The main zone is concentrated, and n-hexane is added to the residue. The precipitated colorless crystals (230 mg, 71%) are isolated. Melting point: 119°-120° C. 1 H-NMR ([D6 ] DMSO): δ=1.09 (d, J=7.0, CH3), 1.15 (d, J=6.9, CH3), 2.45, 2.60, 2.63, 2.89 (4m, CH and Hα, β --C(2')), 4.06 (s, OCH3), 4.18 (m, H--C(5')), 4.28 (m, H--C(4')), 5.35 (m, H--C(3')), 6.47 (m, H--C(1')), 7.58 (s, H--C(6)), 9.45 (d, J=8.9, NH), 10.84 (d, J=9.6, HCO). Anal. calculated for C21H27 CIN4O7 (482.9): C 52.23, H 5.64, N 11.60; found: C 52.51, H 5.69, N 11.65.

Workup

  1. customThe organic layer is separated off
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe evaporated residue is dissolved in CH2Cl2
  7. customthis solution is chromatographed on silica gel (column: 5×20 cm, CH2Cl2 /acetone, 95:5)
  8. concentrationThe main zone is concentrated
  9. additionn-hexane is added to the residue

Sources & evidence

ORD record
ord-93b0b231c15a487dbaf95da096300abc
Source dataset
uspto-grants-1998_12
Patent number
US05844106

Reaction notes

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