Dichloromethane → HCID 86702583, compound

HRID 1746817Notes

Reaction equation

HRID 1746817 reaction equation
ClCCl.[CH3:4][Si:5]([CH3:36])([C:32]([CH3:35])([CH3:34])[CH3:33])[O:6][CH2:7][C@H:8]1[C@H:12]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH2:11][C@@H:10]([OH:20])[C@@H:9]1[CH2:21][CH2:22][C@H:23]([OH:31])[CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28].C(N(CC)CC)C.[S:44](Cl)([CH3:47])(=[O:46])=[O:45]>O>[CH3:36][Si:5]([CH3:4])([C:32]([CH3:33])([CH3:35])[CH3:34])[O:6][CH2:7][C@H:8]1[C@H:12]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH2:11][C@@H:10]([O:20][S:44]([CH3:47])(=[O:46])=[O:45])[C@@H:9]1[CH2:21][CH2:22][C@H:23]([O:31][S:44]([CH3:47])(=[O:46])=[O:45])[CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86702584HCID 86702584, compound

Product 1

HCID 86702583HCID 86702583, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An anhydrous dichloromethane (323 mL) solution of the compound 7 (38.0 g) and triethylamine (44 mL) was cooled to around −60° C. in a dry ice-methanol bath, and mesyl chloride (15 mL) was added dropwise over about 20 minutes. The bath was changed to an ice bath, the mixture was stirred for 2 hours, and the reaction mixture was then added to cold water (600 mL), and extracted with a mixed solution of hexane (600 mL) and ethyl acetate (600 mL). The organic layer was washed with 1 M hydrochloric acid (290 mL) and a saturated saline (300 mL×3 times), dried with anhydrous sodium sulfate, and then concentrated to obtain a titled compound (44.7 g) having the following physical property values.

Workup

  1. customThe bath was changed to an ice bath
  2. extractionextracted with a mixed solution of hexane (600 mL) and ethyl acetate (600 mL)
  3. washThe organic layer was washed with 1 M hydrochloric acid (290 mL)
  4. dry with materiala saturated saline (300 mL×3 times), dried with anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4ac23e71690f43af9ac45d8c45d11767
Source dataset
uspto-grants-2015_10
Patent number
US09150537B2

Reaction notes

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