Acetyl chloride → HCID 68860835, compound

HRID 898876Notes

Reaction equation

HRID 898876 reaction equation
[C:1]([O:5][C:6](=[O:21])[C:7]([S:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH2:16][CH:15]([NH2:20])[CH2:14]2)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[C:22](Cl)(=[O:24])[CH3:23]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:21])[C:7]([S:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH2:16][CH:15]([NH:20][C:22](=[O:24])[CH3:23])[CH2:14]2)([CH3:9])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 68860578HCID 68860578, compound

Product 1

HCID 68860835HCID 68860835, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To 2-(2-aminoindan-5-ylsulfanyl)-2-methylpropionic acid tert-butyl ester (14.6 g; 47.4 mmol), dissolved in CH2Cl2 (100 mL), is added TEA (8.6 mL; 61.7 mmol) and the reaction mixture is cooled to 0° C. Acetyl chloride (4.1 mL; 57.6 mmol) is added dropwise at a rate to maintain the temperature between 0-5° C. The reaction was allowed to warm to RT, stirred for 16 h, diluted with CH2Cl2, washed with H2O, dried over Na2SO4 and evaporated under reduced pressure. The crude oil was purified by flash chromatography (SiO2) eluting with a hexanes-EtOAc gradient to afford 11.7 g (71%) of 2-(2-acetylaminoindan-5-ylsulfanyl)-2-methylpropionic acid tert-butyl ester as a beige solid.

Workup

  1. temperatureto maintain the temperature between 0-5° C
  2. temperatureto warm to RT
  3. washwashed with H2O
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe crude oil was purified by flash chromatography (SiO2)
  7. washeluting with a hexanes-EtOAc gradient

Sources & evidence

ORD record
ord-7f5519f10db2400681289be2bf2ff33a
Source dataset
uspto-grants-2008_04
Patent number
US07351857B2

Reaction notes

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