Chloroacetyl chloride → HCID 118117511, compound

HRID 1747227Notes

Reaction equation

HRID 1747227 reaction equation
[OH-].[Na+].[NH2:3][C:4]([CH3:15])([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([I:14])[CH:9]=1)[CH2:5][OH:6].[Cl:16][CH2:17][C:18](Cl)=[O:19]>C(Cl)Cl>[Cl:16][CH2:17][C:18]([NH:3][C:4]([CH2:5][OH:6])([CH3:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([I:14])[CH:9]=1)=[O:19]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14798Sodium Hydroxide2×HCID 89560151HCID 89560151, compound

Product 1

HCID 118117511HCID 118117511, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
35 °C

Procedure

NaOH 1M aq. soln. (10 mL) followed by NaOH 32% (270 μL) were added to a 0° C. solution of rac-2-amino-3-(3-iodo-phenyl)-2-methyl-propan-1-ol H-6 (850 mg, 2.92 mmol) in DCM (10 mL). After 10 min a solution of chloroacetyl chloride (261 mL, 3.21 mmol) in DCM (10 mL) was added dropwise to the reaction mixture maintaining the temperature below 5° C. The resulting suspension was heated to 35° C. for 30 min after which complete formation of product was observed by LCMS. The layers were separated and the aqueous layer extracted with DCM (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo to give the title compound that was used further without purification. LC-MS A: tR=0.79 min; [M(35Cl)+H]+=367.91.

Workup

  1. temperaturemaintaining the temperature below 5° C
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with DCM (2×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-c051643baa96440b886884fa221d9a87
Source dataset
uspto-grants-2015_10
Patent number
US09150566B2

Reaction notes

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