Dichloromethane → HCID 59830382, compound

HRID 1619736Notes

Reaction equation

HRID 1619736 reaction equation
Cl[C:2]1([CH:8]=[N:9][OH:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH2:3]1.[CH2:11]([N:18]1[CH2:23][CH2:22][C:21](=[CH2:24])[CH:20]([CH3:25])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(Cl)Cl.C(N(CC)CC)C>O>[CH2:11]([N:18]1[CH2:23][CH2:22][C:21]2([O:10][N:9]=[C:8]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:24]2)[CH:20]([CH3:25])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane3×HCID 8471TriethylamineHCID 59830372HCID 59830372, compoundHCID 86624330HCID 86624330, compound

Product 1

HCID 59830382HCID 59830382, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound C (4.49 g, 28.9 mmol, dissolved in abs. DCM (25 ml)) was added dropwise to a solution of compound S (2.5 g, 14.45 mmol) in abs. DCM (25 ml) at 0° C. within 10 min. A solution of triethylamine (16 ml, 11.7 g, 115.6 mmol) in abs. DCM (25 ml) was added to this mixture within 10 min at 0° C. As the reaction was highly exothermic, cooling was carried out in a mixture of ice/sodium chloride. The reaction mixture was stirred for 16 h at RT. For working up the mixture, DCM (50 ml) and water (70 ml) were added. The phases were separated. The aqueous solution was extracted with DCM (2×20 ml). The combined organic phases were washed successively with water (50 ml) and sat. NaCl solution (50 ml) and then dried and concentrated (4.9 g, yellow oil). The residue was purified by column chromatography [silica gel 60 (500 g); EtOAc/cyclohexane 1:2 (3 l)]. The desired product was obtained as a diastereomer mixture in a yield of (2.28 g, 50%) having a melting point of 101-108° C.

Workup

  1. temperaturecooling
  2. additionwere added
  3. customThe phases were separated
  4. extractionThe aqueous solution was extracted with DCM (2×20 ml)
  5. washThe combined organic phases were washed successively with water (50 ml) and sat. NaCl solution (50 ml)
  6. customdried
  7. concentrationconcentrated (4.9 g, yellow oil)
  8. customThe residue was purified by column chromatography [silica gel 60 (500 g); EtOAc/cyclohexane 1:2 (3 l)]

Sources & evidence

ORD record
ord-a8a536cee07b4c40b6573cbcd009182e
Source dataset
uspto-grants-2014_07
Patent number
US08772307B2

Reaction notes

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