Methanol → HCID 178418975, compound

HRID 10516Notes

Reaction equation

HRID 10516 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][S:17](Cl)(=[O:19])=[O:18].CO.O>N1C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([O:15][S:17]([CH3:16])(=[O:19])=[O:18])[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 178418329HCID 178418329, compound

Product 1

HCID 178418975HCID 178418975, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of Intermediate 35 (90.3 g) in pyridine (415 ml) was added dropwise with methanesulfonyl chloride (42.4 ml) with stirring and ice cooling over 15 minutes and stirred with ice cooling for 30 minutes and at room temperature for 20 minutes. The reaction mixture was added with methanol (54.2 ml) to terminate the reaction, stirred at room temperature for 2.5 hours, further added with water (540 ml) and stirred at room temperature for 1 hour and with ice cooling for 1 hour. The deposited precipitates were collected by filtration, washed with water and then dried at 40° C. under reduced pressure to obtain the title compound (105 g).

Workup

  1. stirringstirred with ice cooling for 30 minutes and at room temperature for 20 minutes
  2. customto terminate
  3. customthe reaction
  4. stirringstirred at room temperature for 2.5 hours
  5. stirringstirred at room temperature for 1 hour and with ice cooling for 1 hour
  6. customThe deposited precipitates
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customdried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-d2ae7ccd3f25492baf70cc5fa51d6131
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Reaction notes

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