Chlorosuccinimide → HCID 88180221, compound

HRID 1018039Notes

Reaction equation

HRID 1018039 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:18]2[C:17]([O:19][CH3:20])=[N:16][C:15]([NH:21][CH:22]=[O:23])=[N:14][C:13]=2[N:12]([C@@H:24]2[O:34][C@H:33]([CH2:35][O:36][C:37](=[O:41])[CH:38]([CH3:40])[CH3:39])[C@@H:26]([O:27][C:28](=[O:32])[CH:29]([CH3:31])[CH3:30])[CH2:25]2)[CH:11]=1>C(Cl)Cl>[CH3:30][CH:29]([CH3:31])[C:28]([O:27][C@@H:26]1[C@@H:33]([CH2:35][O:36][C:37](=[O:41])[CH:38]([CH3:40])[CH3:39])[O:34][C@@H:24]([N:12]2[C:13]3[N:14]=[C:15]([NH:21][CH:22]=[O:23])[N:16]=[C:17]([O:19][CH3:20])[C:18]=3[C:10]([Cl:9])=[C:11]2[Cl:1])[CH2:25]1)=[O:32]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 15218404HCID 15218404, compound

Product 1

HCID 88180221HCID 88180221, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Chlorosuccinimide (117 mg, 0.9 mmol) is added to a solution of compound (45) (200 mg, 0.4 mmol in 5 ml of DMF). After it had been stirred (at room temperature for 16 h), the solution is added to a mixture of CH2Cl2/5% aq. NaHCO3 (50 ml, 9:1). The organic phase 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 separated off. Colorless crystals (149 mg, 72%) are obtained after evaporating off the solvent and crystallizing from cyclohexane. Melting point: 127-128° C. 1H-NMR ([D6] DMSO): δ=1.01 (dd, CH3), 1.14 (d, J=7.0, CH3), 2.44, 2.47, 2.60, 3.53 (4 m, CH and Hα,β—C(2′)), 4.05 (s, OCH3), 4.17 (m, H—C(5′)), 4.30 (m, H—C(4′)), 5.56 (m, H—C(3′)), 6.41 (m, H—C(1′)), 9.44 (d, J=9.1, NH), 10.94 (d, J=9.8, HCO). Anal. calculated for C21H26Cl2N4O7 (517.4): C 48.75, H 5.07, N 10.83; found: C 49.04, H 5.09, N 10.66.

Workup

  1. customThe organic phase 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. customThe main zone is separated off

Sources & evidence

ORD record
ord-5e7dab5d6c5f40ea80072b90e2b0f2d1
Source dataset
uspto-grants-2002_11
Patent number
US06479651B1

Reaction notes

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