Dichloromethane → HCID 59837324, compound

HRID 2356232Notes

Reaction equation

HRID 2356232 reaction equation
C(Cl)Cl.[CH2:4]([O:11][C:12]1[CH:13]=[C:14]([S:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])([CH2:30][O:31][CH2:32][O:33][CH3:34])[CH2:28][OH:29])=[C:21]([Cl:43])[CH:20]=2)[CH:15]=[CH:16][CH:17]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(Br)(Br)(Br)Br.[P:49]([O:54]C)([O:52][CH3:53])[O:50][CH3:51]>O.N1C=CC=CC=1>[CH2:4]([O:11][C:12]1[CH:13]=[C:14]([S:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([NH:35][C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])([CH2:30][O:31][CH2:32][O:33][CH3:34])[CH2:28][O:29][P:49]([O:52][CH3:53])([O:50][CH3:51])=[O:54])=[C:21]([Cl:43])[CH:20]=2)[CH:15]=[CH:16][CH:17]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8472Trimethyl phosphiteHCID 11205Carbon tetrabromideHCID 59837290HCID 59837290, compound

Product 1

HCID 59837324HCID 59837324, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a methylene chloride solution (2 mL) containing the compound of Example 219 (860 mg), carbon tetrabromide (533 mg) and pyridine (2 mL), trimethyl phosphite (0.19 mL) was added while the mixture was stirred at 0° C. and the mixture was stirred for 5 hours until room temperature. Subsequently, water was added and the mixture was extracted with ethyl acetate. The extract was washed sequentially with water and a saturated aqueous solution of sodium chloride. The organic phase was then dried over anhydrous sodium sulfate. The solvent was removed by distillation and the residue was purified on a silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain the desired product as a colorless oil (830 mg).

Workup

  1. additionwas added while the mixture
  2. stirringthe mixture was stirred for 5 hours until room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed sequentially with water
  5. dry with materialThe organic phase was then dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation
  7. customthe residue was purified on a silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-3c20a78fa3c14d0893c8348ed1dd258f
Source dataset
uspto-grants-2010_07
Patent number
US07759326B2

Reaction notes

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