Benzenesulfonyl chloride → HCID 69414949, compound

HRID 1350914Notes

Reaction equation

HRID 1350914 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[CH:13]=[C:14]([C@@H:26]([OH:45])[CH2:27][NH:28][C:29]([CH3:44])([CH3:43])[CH2:30][CH2:31][N:32]2[CH:36]=[C:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[N:34]=[CH:33]2)[CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>N1C=CC=CC=1>[CH2:19]([O:18][C:17]1[CH:16]=[CH:15][C:14]([C@@H:26]([OH:45])[CH2:27][NH:28][C:29]([CH3:44])([CH3:43])[CH2:30][CH2:31][N:32]2[CH:36]=[C:35]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[N:34]=[CH:33]2)=[CH:13][C:12]=1[NH:11][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 69414844HCID 69414844, compound

Product 1

HCID 69414949HCID 69414949, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

0.10 mL (41 mmol) benzenesulphonic acid chloride were slowly added at 0° C. to a solution of 0.20 g (41 mmol) (R)-1-(3-amino-4-benzyloxyphenyl)-2-[1,1-dimethyl-3-(4-phenylimidazol-1-yl)-propylamino]-ethanol in 5 mL pyridine with vigorous stirring. After the addition was complete the reaction mixture was stirred for 4 h at 0° C. and then poured into 40 mL ice water/ethyl acetate (1:1). The phases were separated and the aqueous phase was extracted three times with 20 mL of ethyl acetate. The combined organic phases were dried over magnesium sulphate and the solvent was removed using the rotary evaporator. 0.14 g (0.28 mmol, 99%) (R)—N-(2-benzyloxy-5-{2-[1,1-dimethyl-3-(4-phenylimidazol-1-yl)-propylamino]-1-hydroxyethyl}-phenyl)-benzenesulphonamide was obtained as a white solid.

Workup

  1. additionAfter the addition
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted three times with 20 mL of ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. customthe solvent was removed
  6. customthe rotary evaporator

Sources & evidence

ORD record
ord-9dcd8ea058824a418414a02346c7ff13
Source dataset
uspto-grants-2007_05
Patent number
US07214698B2

Reaction notes

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