Benzo(d)thiazol-2-amine → HCID 67711381, compound

HRID 974865Notes

Reaction equation

HRID 974865 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([C:23]1(C(O)=O)[NH:28][C:27](=[O:29])[CH:26]([CH2:30][CH:31]([CH3:33])[CH3:32])[N:25]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:24]1=[O:42])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O[N:47]1[C:51](=[O:52])CCC1=O.N[C:55]1[S:56][C:57]2[CH:63]=[CH:62][CH:61]=[CH:60][C:58]=2[N:59]=1>O1CCOCC1.C(OCC)(=O)C>[S:56]1[C:57]2[CH:63]=[CH:62][CH:61]=[CH:60][C:58]=2[N:59]=[C:55]1[C:23]1([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:28]([C:51](=[O:52])[NH2:47])[C:27](=[O:29])[CH:26]([CH2:30][CH:31]([CH3:33])[CH3:32])[N:25]([O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:24]1=[O:42]

Participants

7

Reactant 4

HCID 8706Benzo(d)thiazol-2-amineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 19969579HCID 19969579, compound

Product 1

HCID 67711381HCID 67711381, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

1.09 g of dicyclohexylcarbodiimide was added to 25 ml of a solution of 2.17 g of (3RS,6SR)-3-benzyl-1-benzyloxy-3-carboxy-6-isobutylpiperazine-2,5-dione and 0.63 g of N-hydroxysuccinimide in anhydrous dioxane. The mixture was stirred at room temperature for 2 hours. Thereto was added 0.80 g of 2-aminobenzothiazole. The mixture was stirred at room temperature for 23 hours. The reaction mixture was diluted with 200 ml of ethyl acetate. The resulting solution was washed with an aqueous solution saturated with sodium hydrogen carbonate and an aqueous solution saturated with sodium chloride, then dried with anhydrous magnesium sulfate, and subjected to distillation to remove the solvent. The residue was crystallized using ethyl acetate, to obtain 2.77 g of (3RS,6SR)-3-(benzothiazol-2-yl)-carbamoyl-3-benzyl-1-benzyloxy-6-isobutylpiperazine-2,5-dione as a white solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 23 hours
  2. washThe resulting solution was washed with an aqueous solution saturated with sodium hydrogen carbonate
  3. dry with materialan aqueous solution saturated with sodium chloride, then dried with anhydrous magnesium sulfate
  4. distillationsubjected to distillation
  5. customto remove the solvent
  6. customThe residue was crystallized

Sources & evidence

ORD record
ord-0c6600db53ac42138207b9989ff91584
Source dataset
uspto-grants-1997_03
Patent number
US05607934

Reaction notes

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