Triethylamine → HCID 22557737, compound

HRID 984063Notes

Reaction equation

HRID 984063 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.[CH2:27]([S:31](Cl)(=[O:33])=[O:32])[CH2:28][CH2:29][CH3:30]>C(Cl)Cl>[C:1]([OH:4])(=[O:3])[CH3:2].[CH2:13]([O:12][C:11]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:5][S:31]([CH2:27][CH2:28][CH2:29][CH3:30])(=[O:33])=[O:32])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 754301-Butanesulfonyl chlorideHCID 69680486HCID 69680486, compound

Product 1

HCID 22557737HCID 22557737, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

5.0 g (0.00194 mol) of 3-amino-4-benzyloxybenzene acetate are mixed under a nitrogen atmosphere in 15 ml of methylene chloride, and 3.3 ml of triethylamine (0.0236 mol) and 3.3 ml (0.0245 mol) of 1-butansulfonyl chloride are added thereto. The mixture is stirred at ambient temperature overnight and afterwards at 30° C. for 4 hours. Washing with water is carried out, the two phases are separated, the organic phase is dried over sodium sulfate and filtered, and the solvent is evaporated under reduced pressure. Purification is carried out by chromatography on a column of silica gel, elution being carried out with a cyclohexane/ethyl acetate=9:1 mixture. The title compound is obtained.

Workup

  1. washWashing with water
  2. customthe two phases are separated
  3. dry with materialthe organic phase is dried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent is evaporated under reduced pressure
  6. customPurification
  7. washis carried out by chromatography on a column of silica gel, elution

Sources & evidence

ORD record
ord-a577057633374760970b46baa227988a
Source dataset
uspto-grants-2005_03
Patent number
US06867220B2

Reaction notes

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