Isopropylamine → HCID 53826697, compound

HRID 1734665Notes

Reaction equation

HRID 1734665 reaction equation
C([O:4][CH:5]1[CH:9]([N:10]2[C:14]3[CH:15]=[C:16]([Cl:20])[C:17]([Cl:19])=[CH:18][C:13]=3[N:12]=[C:11]2Br)[CH2:8][CH:7]([CH2:22][O:23]C(=O)C)[CH:6]1[O:27]C(=O)C)(=O)C.[CH:31]([NH2:34])([CH3:33])[CH3:32]>C(O)C>[Cl:19][C:17]1[C:16]([Cl:20])=[CH:15][C:14]2[N:10]([CH:9]3[CH:5]([OH:4])[CH:6]([OH:27])[CH:7]([CH2:22][OH:23])[CH2:8]3)[C:11]([NH:34][CH:31]([CH3:33])[CH3:32])=[N:12][C:13]=2[CH:18]=1

Participants

4

Reactant 2

HCID 6363Isopropylamine2×HCID 54404171HCID 54404171, compound

Product 1

HCID 53826697HCID 53826697, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(±)-(1R*, 2S*, 3S*, 5S*)-3-(Acetoxymethyl)-5-(2-bromo-5,6-dichloro-1H-benzimidazol-1-yl)-1,2-cyclopentanediyl diacetate (750 mg, 1.44 mmole) was refluxed in ethanol (10 mL) with isopropylamine (1.22 mL, Aldrich) under nitrogen for 18 hours. A second portion of isopropylamine (1.22 mL) was added and reflux continued for an additional 24 hours. Volatiles were evaporated, the residue was redissolved in ethanol, 1N sodium hydroxide (1.44 mL) was added, and volatiles were reevaporated. The residue was chromatographed on a silica gel column. Title compound was eluted with 10% methanol-chloroform as a colorless glass. The glass was crystallized from ethyl acetate-hexanes to give (±)-(1R*, 2S*, 3S*, 5S*)-5-[5,6-dichloro-2-(isopropylamino)-1H-benzimidazol-1-yl]-3-(hydroxymethyl)-1,2-cyclopentanediol as white crystals (305 mg, 57%); m.p. 213°-214° C.; 1H-NMR(DMSO-d6) identical with that of the enantiomer described in Example 75.

Workup

  1. temperaturereflux
  2. customVolatiles were evaporated
  3. dissolutionthe residue was redissolved in ethanol
  4. addition1N sodium hydroxide (1.44 mL) was added
  5. customvolatiles were reevaporated
  6. customThe residue was chromatographed on a silica gel column
  7. washTitle compound was eluted with 10% methanol-chloroform as a colorless glass
  8. customThe glass was crystallized from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-f987973663b14683ac4b0d18b85229ee
Source dataset
uspto-grants-1996_07
Patent number
US05534535

Reaction notes

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