Water → HCID 19766961, compound

HRID 1591407Notes

Reaction equation

HRID 1591407 reaction equation
C(=O)([O-])[O-].[K+].[K+].O.[NH2:8][CH:9]1[CH2:18][CH2:17][C:16]2[CH:15]=[C:14]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:13]=[CH:12][C:11]=2[CH2:10]1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>C(OCC)(=O)C>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:8][CH:9]2[CH2:18][CH2:17][C:16]3[CH:15]=[C:14]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:13]=[CH:12][C:11]=3[CH2:10]2)(=[O:34])=[O:33])=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73984-Chlorobenzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 19766966HCID 19766966, compound

Product 1

HCID 19766961HCID 19766961, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

2.99 g of potassium carbonate, 20 ml of ethyl acetate and 40 ml of water are added to 2.09 g of ethyl (+)-6-amino-5,6,7,8-tetrahydronaphthalene-2-acetate 1/2 (+)-D-dibenzoyltartrate, and a solution of 1.28 g of 4-chlorophenylsulfonyl chloride in 20 ml of ethyl acetate is added thereto at room temperature under stirring. After the mixture is stirred at room temperature for 1.5 hour, the organic layer is separated therefrom, washed, dried and evaporated to revove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform) to give 2.10 g of ethyl (+)-6-(4-chlorophenyl)sulfonylamino-5,6,7,8-tetrahydronaphthalene-2-acetate as colorless viscous oil.

Workup

  1. stirringAfter the mixture is stirred at room temperature for 1.5 hour
  2. customthe organic layer is separated
  3. washwashed
  4. customdried
  5. customevaporated
  6. customThe residue is purified by silica gel column chromatography (solvent; chloroform)

Sources & evidence

ORD record
ord-b92e9c04010344eca25aa21d712a7ba9
Source dataset
uspto-grants-1993_04
Patent number
US05206428

Reaction notes

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