Benzyltrimethylammoniumtribromide → HCID 86654764, compound

HRID 447140Notes

Reaction equation

HRID 447140 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[S:27])[NH:11][CH2:12][CH2:13][NH:14][C:15](=[O:26])[C@H:16]([NH:19][C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])[CH2:17][CH3:18])=[CH:5][CH:4]=1.[Br-].[Br-].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:9]=[C:10]([NH:11][CH2:12][CH2:13][NH:14][C:15](=[O:26])[C@@H:16]([NH:19][C:20](=[O:25])[C:21]([F:22])([F:23])[F:24])[CH2:17][CH3:18])[S:27][C:7]=2[CH:8]=1

Participants

4

Reactant 2

HCID 53442637BenzyltrimethylammoniumtribromideHCID 86654763HCID 86654763, compound

Product 1

HCID 86654764HCID 86654764, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)—N-(2-(3-(4-methoxyphenyl)thioureido)ethyl)-2-(2,2,2-trifluoroacetamido)butanamide (412.5 mgs, 1.0 mmol) in methylene chloride (10 mL) was treated with benzyltrimethylammonium tribromide (389.4 mgs 1.00 mmol) and the resulting mixture stirred overnight. The reaction was then quenched with aqueous sodium bicarbonate and extracted into methylene chloride. The organic layer was dried over sodium sulfate, then filtered and concentrated to yield a residue which was purified by normal phase column chromatography, eluting with 5% methanol in chloroform to yield (S)—N-(2-(6-methoxybenzo[d]thiazol-2-ylamino)ethyl)-2-(2,2,2-trifluoroacetamido)-butanamide as a yellow solid.

Workup

  1. customThe reaction was then quenched with aqueous sodium bicarbonate
  2. extractionextracted into methylene chloride
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a residue which
  7. customwas purified by normal phase column chromatography
  8. washeluting with 5% methanol in chloroform

Sources & evidence

ORD record
ord-0f03b451ea984a578bedf89d4313dbb7
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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