Isopropylamine → HCID 53826697, compound

HRID 1416442Notes

Reaction equation

HRID 1416442 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, 1 N 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 23 .[See Examples 1-4]

Workup

  1. temperaturereflux
  2. customVolatiles were evaporated
  3. dissolutionthe residue was redissolved in ethanol
  4. addition1 N 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

Sources & evidence

ORD record
ord-99e7d7f8f6c04c088bfa52a2ebb45cab
Source dataset
uspto-grants-1999_06
Patent number
US05912356

Reaction notes

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