Water → HCID 13852701, compound

HRID 2231833Notes

Reaction equation

HRID 2231833 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][CH2:12][NH:11][C:10](=[O:14])[C@H:9]2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:4][CH:3]=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23].O>N1C=CC=CC=1>[S:22]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][CH2:12][NH:11][C:10](=[O:14])[C@H:9]2[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:4][CH:3]=1)([CH3:21])(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 13852697HCID 13852697, compound

Product 1

HCID 13852701HCID 13852701, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.34 g (0.005 mol) of 27 in 10 cm3 of anhydrous pyridine, 1.14 g (0.01 mol; 0.77 cm3) of methanesulfonyl chloride are added under an atmosphere of nitrogen at 0° C. The mixture is stirred for 1 hour at between 0° and 3° C. before being poured into 70 cm3 of cold water. This mixture is extracted with methylene chloride and washed to neutrality. After evaporation and recrystallization in methanol, 29 is obtained in 61% yield. M.p. 199° C.

Workup

  1. extractionThis mixture is extracted with methylene chloride
  2. washwashed to neutrality
  3. customAfter evaporation and recrystallization in methanol
  4. custom29 is obtained in 61% yield

Sources & evidence

ORD record
ord-2abf962d2ed341f2bca40f6cf842a7c9
Source dataset
uspto-grants-1988_11
Patent number
US04785007

Reaction notes

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