Dichloromethane → HCID 69029027, compound

HRID 2112567Notes

Reaction equation

HRID 2112567 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C@@H:6]1[C@@H:14]([O:15][CH2:16][CH2:17][CH2:18][NH2:19])[C@@H:13]([O:20][CH2:21][CH2:22][CH2:23][NH2:24])[C@@H:12]([CH2:25][O:26][CH2:27][CH2:28][CH2:29][NH2:30])[O:11][C@@H:7]1[O:8][CH2:9][CH3:10].[C:31]([O-:34])(O)=O.[Na+].COC([C:40]1[C:41](N[C:44](=[O:46])[CH:45]=1)=[O:42])=O.C(Cl)Cl>O.C(#N)C>[C:31]1(=[O:34])[N:1]([CH2:2][CH2:3][CH2:4][O:5][C@@H:6]2[C@@H:14]([O:15][CH2:16][CH2:17][CH2:18][N:19]3[C:41](=[O:42])[CH:40]=[CH:45][C:44]3=[O:46])[C@@H:13]([O:20][CH2:21][CH2:22][CH2:23][N:24]3[C:6](=[O:5])[CH:14]=[CH:13][C:12]3=[O:11])[C@@H:12]([CH2:25][O:26][CH2:27][CH2:28][CH2:29][N:30]3[C:41](=[O:42])[CH:40]=[CH:45][C:44]3=[O:46])[O:11][C@@H:7]2[O:8][CH2:9][CH3:10])[C:16](=[O:15])[CH:17]=[CH:18]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 22289804HCID 22289804, compoundHCID 69030403HCID 69030403, compound

Product 1

HCID 69029027HCID 69029027, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of amine 6 (17.8 mg, 0.04 mmol) in 1 M aqueous solution of NaHCO3 (1 mL) was treated with methoxycarbonylmaleimide (37.94 mg, 0.24 mmol) at 0° C. After 5 min, the mixture was diluted with water (1 mL) and acetonitrile (2 mL), and then stirred at room temperature for 4 h. After adding CH2Cl2 (50 mL), the organic layer was separated and washed with brine (3×10 mL). The organic layer was then dried (Na2SO4), filtered, and concentrated. The oily residue was purified by flash chromatography (CH2Cl2/MeOH 95:5) to give maleimide 7 (23.2 mg, 76%); Rf 0.42 (CH2Cl2/MeOH 95:5); 1H-NMR (CDCl3/TMS): δ6.70 (s, 2H, CH═CH), 6.69 (s, 4H, CH═CH), 6.68 (s, 2H, CH═CH), 4.98 (d, 1H, J=3.4 Hz, H-1), 3.95-3.82 (m, 2H, H-4, and OCHHCH2CH2N), 3.80˜3.35 (m, 22H, H-2, H-3, H-5, H-6, H-6′, OCH2CH2CH2N, OCH2CH2CH2N, and OCH2CH3), 1.96-1.78 (m, 8H, OCH2CH2CH2N), 1.25 (t, 3H, J=7.1 Hz, OCH2CH3); ES-MS: 779.28 (M+Na)+, 401.29 (M+2Na)2+.

Workup

  1. customthe organic layer was separated
  2. washwashed with brine (3×10 mL)
  3. dry with materialThe organic layer was then dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe oily residue was purified by flash chromatography (CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-30ba2284be644f268f28c98a88c19b36
Source dataset
uspto-grants-2009_04
Patent number
US07524821B2

Reaction notes

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