Chlorosuccinimide → HCID 86618577, compound

HRID 1436366Notes

Reaction equation

HRID 1436366 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[C:18]([NH:21][C@@H:22]([CH2:25][CH3:26])[CH2:23][OH:24])[S:19][CH:20]=2)=[CH:12][CH:11]=1>C(Cl)Cl>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[N:17]=[C:18]([NH:21][C@@H:22]([CH2:25][CH3:26])[CH2:23][OH:24])[S:19][C:20]=2[Cl:1])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 86618578HCID 86618578, compound

Product 1

HCID 86618577HCID 86618577, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-chlorosuccinimide (975.0 mg, 7.30 mmol) in 50 mL of methylene chloride was added under nitrogen at room temperature dropwise over 45 min to a solution of (2S)-2-{[4-(4-bromophenyl)-1,3-thiazol-2-yl]amino}butan-1-ol (2.1611 g, 6.60 mmol), prepared in step 1 of Example 7, in 50 mL of methylene chloride. After the addition, the reaction was stirred at room temperature for 3 h. The reaction was poured directly onto a column of silica gel (230-400 mesh). Elution of the column with 5% ethyl acetate-methylene chloride to 15% ethyl acetate-methylene chloride gave (2S)-2-{[4-(4-bromophenyl)-5-chloro-1,3-thiazol-2-yl]amino}butan-1-ol (1.5371 g, 64%) as a yellow foam, MS (ES) m/z 358.8 [M+H]+.

Workup

  1. additionAfter the addition
  2. additionThe reaction was poured directly onto a column of silica gel (230-400 mesh)
  3. washElution of the column with 5% ethyl acetate-methylene chloride to 15% ethyl acetate-methylene chloride

Sources & evidence

ORD record
ord-1dd8d365a2ac4ebfbfe8ba25810de6dc
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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