Hydrochloric Acid → HCID 11245479, compound

HRID 2054737Notes

Reaction equation

HRID 2054737 reaction equation
[Br:1][CH2:2][C:3]([OH:5])=O.Cl[C:7]([O:9][CH2:10][CH3:11])=O.COC1C=CC([C:20]2[C:25]([S:26]([NH2:29])(=[O:28])=[O:27])=CC=[CH:22][C:21]=2[CH2:30][C@H:31]([NH2:33])[CH3:32])=CC=1.Cl>C(Cl)Cl.C(N(CC)CC)C>[Br:1][CH2:2][C:3]([NH:33][C@H:31]([CH3:32])[CH2:30][C:21]1[CH:22]=[CH:11][C:10]([O:9][CH3:7])=[C:25]([S:26]([NH2:29])(=[O:27])=[O:28])[CH:20]=1)=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6227Bromoacetic AcidHCID 10928Ethyl chloroformateHCID 69295014HCID 69295014, compound

Product 1

HCID 11245479HCID 11245479, compoundYield 117%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
-42.5 °C

Procedure

Bromoacetic acid (3.4 g) was dissolved in 50 ml of methylene chloride. 2.3 g of triethyamine was added to the resultant solution and cooled to −40 to −45° C. Then, 2.66 g of ethyl chloroformate was added dropwise to the resultant solution and stirred at −40 to −45° C. for 4 hours. 3.0 g of (R)-2-(4-methoxyphenyl-3-aminosulfonyl-phenyl)-1-methylethylamine was added to the resultant product and stirred at −40 to −45° C. for 1.5 hours. Then, 50 ml of 10% HCl were added to the resultant solution and stirred. The organic layer was separated and washed with 50 ml of 10% K2CO3 solution and dried over MgSO4, and then, filtered and concentrated. The obtained concentrate was dissolved in methanol and recrystallized with hexane to obtain the title compound as a white solid (4.0 g).

Workup

  1. stirringstirred at −40 to −45° C. for 1.5 hours
  2. stirringstirred
  3. customThe organic layer was separated
  4. washwashed with 50 ml of 10% K2CO3 solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. concentrationThe obtained concentrate
  9. dissolutionwas dissolved in methanol
  10. customrecrystallized with hexane

Sources & evidence

ORD record
ord-eaacd5416713487f81dc0dc777bb8e1c
Source dataset
uspto-grants-2008_02
Patent number
US07329780B2

Reaction notes

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