Water → HCID 19975167, compound

HRID 1450143Notes

Reaction equation

HRID 1450143 reaction equation
Br.[CH2:2]([C:4]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:9](=[O:10])[N:8]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[O:16])[C:7](=[O:23])[NH:6][C:5]1=[O:24])[CH3:3].[C:31]1(=[O:37])[O:36][C:34](=[O:35])[CH2:33][CH2:32]1.C(N(CC)CC)C.O>C(Cl)(Cl)Cl.ClCCl>[C:34]([CH2:33][CH2:32][C:31]([N:20]1[CH2:21][CH2:22][N:17]([C:15]([CH2:14][CH2:13][CH2:12][CH2:11][N:8]2[C:9](=[O:10])[C:4]([CH2:2][CH3:3])([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:5](=[O:24])[NH:6][C:7]2=[O:23])=[O:16])[CH2:18][CH2:19]1)=[O:37])([OH:36])=[O:35]

Participants

7

Reactant 4

HCID 962WaterHCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 19975173HCID 19975173, compound

Product 1

HCID 19975167HCID 19975167, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

The amine of step 5 (4.8 g, 0.01 mole), succinic anhydride (1.2 g, 0.012 mole), and triethylamine (2.2 g, 0.02 mole) in chloroform (150 mL) were heated for 30 min at 50°-60° C. (hot water) and allowed to stir at ambient temperature for 16 hrs. Dichloromethane (200 mL) was added, the mixture was washed with 10% hydrochloric acid solution (3×100 mL). saturated sodium chloride solution (100 mL), dried over anhydrous magnesium sulfate, filtered, and the solvent removed on a rotary evaporator in vacuo to give a white solid, 3.3 g (66%). This material was chromatographed using a SiO2 column to give a white solid.

Workup

  1. washthe mixture was washed with 10% hydrochloric acid solution (3×100 mL)
  2. dry with materialsaturated sodium chloride solution (100 mL), dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent removed on a rotary evaporator in vacuo
  5. customto give a white solid, 3.3 g (66%)
  6. customThis material was chromatographed
  7. customto give a white solid

Sources & evidence

ORD record
ord-c870b756fcd146eeab0564ce808a2753
Source dataset
uspto-grants-1997_02
Patent number
US05601994

Reaction notes

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