Ethanol → HCID 86754115, compound

HRID 1416437Notes

Reaction equation

HRID 1416437 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][CH2:7][CH:6]1[O:22]C(=O)C)(=O)C.[CH2:26]([OH:28])C.[CH:29]1([NH2:32])[CH2:31][CH2:30]1.[OH-].[Na+]>O.CO.CO.C(Cl)(Cl)Cl>[Cl:19][C:17]1[C:16]([Cl:20])=[CH:15][C:14]2[N:10]([C@H:9]3[C@H:5]([OH:4])[C@H:6]([OH:22])[C@@H:7]([CH2:26][OH:28])[CH2:8]3)[C:11]([NH:32][CH:29]3[CH2:31][CH2:30]3)=[N:12][C:13]=2[CH:18]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 69828CyclopropylamineHCID 76414631HCID 76414631, compound

Product 1

HCID 86754115HCID 86754115, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 21584188Chloroform methanolSolvent

Procedure

(1S, 2R, 3R, 5R)-3-Acetoxymethyl)-5-(2-bromo-5,6-dichloro-1-H-benzimidazol-1-yl)-1,2-cyclopentanediyl diacetate (500 mg 0.958 mmole) was refluxed in water: ethanol/2:1 (7.5 mL) with cyclopropylamine (0.66 mL, 9.6 mmole) under nitrogen for 18 hours. TLC (silica gel, 10% methanol-chloroform) showed complete conversion to a single spot with lower Rf than starting material. 1 N sodium hydroxide (0.96 mL) was added and volatiles were evaporated. The residue was chromatographed on a silica gel flash column. Title compound was eluted with 10% methanol-chloroform as a colorless glass which solidified from water:ethanol/2:1 (5 mL) to give off-white powder (207 mg, 59%, m.p. 116-118° C. dec.; 1H-NMR(DMSO-d6)δ and mass spectrum: identical with those of enantiomer described in Example 74; [α]20589 -12.2°, [α]20578 -12.5°, [α]20546 -13.5° (c=0.312, methanol).

Workup

  1. customvolatiles were evaporated
  2. customThe residue was chromatographed on a silica gel flash column
  3. washTitle compound was eluted with 10% methanol-chloroform as a colorless glass which
  4. customethanol/2:1 (5 mL) to give off-white powder (207 mg, 59%, m.p. 116-118° C. dec.

Sources & evidence

ORD record
ord-6a910247b6e94cea9aabf0a9acdb8ba0
Source dataset
uspto-grants-1999_06
Patent number
US05912356

Reaction notes

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