Dichloromethane → HCID 67085325, compound

HRID 1047462Notes

Reaction equation

HRID 1047462 reaction equation
[C:1]([Si:5]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[O:6][CH:7]1[CH2:11][CH2:10][CH:9]([OH:12])[CH:8]1[CH2:13][O:14][C:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.C(N(CC)C(C)C)(C)C>CS(C)=O.N1C=CC=CC=1>[C:1]([Si:5]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[O:6][CH:7]1[CH2:11][CH2:10][C:9](=[O:12])[CH:8]1[CH2:13][O:14][C:15]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 67085175HCID 67085175, compound

Product 1

HCID 67085325HCID 67085325, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 1049PyridineSolvent2×

Conditions

Temperature
0 °C

Procedure

The compound of formula (XIII) obtained in Example 2-1 (60 g, 97.9 mmol) was mixed with DMSO (36 ml) and methylene chloride (300 ml). The resulting solution was cooled to 0° C. and N,N-diisopropylethylamine (DIPEA) (59.7 ml, 0.343 mol) was added thereto, followed by adding a mixture solution of pyridine.SO3 complex (31.2 g), pyridine (15.9 ml) and DMSO (36 ml). The mixture thus obtained was stirred for 30 min. After completion of the reaction, the organic layer thus obtained was washed with saturated ammonium chloride (300 ml), 2M HCl solution (300 ml), sodium bicarbonate solution (300 ml) and brine (300 ml) respectively, dried over anhydrous sodium sulfate, filtered, and condensed under a reduced pressure to obtain the title compound (60 g, yield: 99%).

Workup

  1. customThe mixture thus obtained
  2. customAfter completion of the reaction
  3. customthe organic layer thus obtained
  4. washwas washed with saturated ammonium chloride (300 ml), 2M HCl solution (300 ml), sodium bicarbonate solution (300 ml) and brine (300 ml) respectively
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customcondensed under a reduced pressure

Sources & evidence

ORD record
ord-74f4ad0da718455d9f27ddd50f18ecda
Source dataset
uspto-grants-2013_10
Patent number
US08569491B2

Reaction notes

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