Acetone → 4-[[[4-(hexahydro-1H-azepin-1-yl)-phenyl]-sulphonyl]-amino]-3-hydroxy butanoic acid

HRID 1590589Notes

Reaction equation

HRID 1590589 reaction equation
[N:1]1([C:8]2[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(C)=O.[OH:22][CH:23]([CH2:28][NH2:29])[CH2:24][C:25]([OH:27])=[O:26].N12CCN(CC1)CC2>O>[N:1]1([C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH:29][CH2:28][CH:23]([OH:22])[CH2:24][C:25]([OH:27])=[O:26])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 21494-Amino-3-hydroxybutanoic acidHCID 9237DabcoHCID 10355958(4-Hexahydro-azepin-1-yl-benzenesulphonyl) chloride

Product 1

HCID 541188884-[[[4-(hexahydro-1H-azepin-1-yl)-phenyl]-sulphonyl]-amino]-3-hydroxy butanoic acidYield 150.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

4.1 g of (4-hexahydro-azepin-1-yl-benzenesulphonyl) chloride then 12 cm3 of acetone are added to a solution of 1.4 g of 3-hydroxy-4-amino butanoic acid and 3.36 g of 1,4-diazabicyclo [2.2.2]octane (DABCO) in 18 cm3 of water. Agitation is carried out for 6 hours at ambient temperature, the acetone is evaporated off, the residue is cooled down to 0° C. and 7.5 cm3 of 2N hydrochloric acid is added. Extraction is carried out with chloroform, the extracts are dried and evaporated to dryness. 6.3 g of desired product is obtained, used as it is for the following stage.

Workup

  1. customthe acetone is evaporated off
  2. addition7.5 cm3 of 2N hydrochloric acid is added
  3. extractionExtraction
  4. customthe extracts are dried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-903cc4cb070b497ea3faf895e944aac8
Source dataset
uspto-grants-1993_04
Patent number
US05204341

Reaction notes

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