Dichloromethane → HCID 131728054, compound

HRID 642936Notes

Reaction equation

HRID 642936 reaction equation
[C:1]([Si:5]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[O:6][CH:7]1[C:11]([C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:17][SiH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])([CH2:12][O:13][N:14]=[CH2:15])[O:10][CH:9]([N:35]2[CH:40]=[CH:39][C:38](=[O:41])[NH:37][C:36]2=[O:42])[CH:8]1[OH:43])([CH3:4])([CH3:3])[CH3:2].ClCCl.[CH3:59][S:60](Cl)(=[O:62])=[O:61]>N1C=CC=CC=1>[C:1]([Si:5]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1)[O:6][CH:7]1[C:11]([C:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:17][SiH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])([CH2:12][O:13][N:14]=[CH2:15])[O:10][CH:9]([N:35]2[CH:40]=[CH:39][C:38](=[O:41])[NH:37][C:36]2=[O:42])[CH:8]1[O:43][S:60]([CH3:59])(=[O:62])=[O:61])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 131728052HCID 131728052, compound

Product 1

HCID 131728054HCID 131728054, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The mesylation of hydroxyl groups proceeds readily under these conditions (Protective Groups in Organic Synthesis, 3rd edition, 1999, pp. 150-160 and references cited therein). Briefly, to a solution of Compound 17 in a 1:1 mixture of anhydrous dichloromethane and anhydrous pyridine is added methanesulfonyl chloride (1.2 eq.). After stirring at room temperature for several hours, this mixture is quenched with methanol, concentrated, diluted with dichloromethane, washed with aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, filtered and evaporated. Purification by silica gel chromatography will yield Compound 18.

Workup

  1. customin Organic Synthesis, 3rd edition, 1999
  2. customthis mixture is quenched with methanol
  3. concentrationconcentrated
  4. additiondiluted with dichloromethane
  5. washwashed with aqueous NaHCO3 and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-f547aaefa0ad4d80bfb07a9a18d85301
Source dataset
uspto-grants-2010_04
Patent number
US07696345B2

Reaction notes

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