Hydrochloric Acid → HCID 69890832, compound

HRID 353372Notes

Reaction equation

HRID 353372 reaction equation
C[O:2][C:3]([C@:5]12[CH2:11][C@@H:8]3[CH2:9][C@H:10]1[C@H:6]2[C@@:7]3([NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C:12]([O:14]C)=[O:13])=[O:4].CO.Cl>O1CCCC1.[OH-].[Na+]>[CH2:20]([O:19][C:17]([NH:16][C@:7]1([C:12]([OH:14])=[O:13])[C@@H:8]2[CH2:11][C@@:5]3([C:3]([OH:4])=[O:2])[C@@H:10]([CH2:9]2)[C@@H:6]13)=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 69891424HCID 69891424, compound

Product 1

HCID 69890832HCID 69890832, compoundYield 64.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 2.0 g (5.6 mmole) of (+/−)-(1R*,2R*,3R*,4S*,6S*)-3-benzyloxycarbonylamino-tricyclo[2.2.1.02,6]heptane-1,3-dicarboxylic acid dimethyl ester in a mixture of 30 mL of tetrahydrofuran and 30 mL of 1 N aqueous sodium hydroxide was stirred at room temperature for 24 hours. Because the starting material was unchanged, methanol was added until homogeneity was achieved and the solution was refluxed under nitrogen for 15 hours. The mixture was acidified with concentrated HCl and extracted with ethyl acetate (2×200 mL). The extract was washed with 200 mL portions of water and saturated brine, dried over sodium sulfate, filtered and concentrated in vacuum. The resulting residue was recrystallized from ethyl acetate/hexane to give 1.2 g of the title compound as a white solid, m.p. 205° C.

Workup

  1. temperaturethe solution was refluxed under nitrogen for 15 hours
  2. extractionextracted with ethyl acetate (2×200 mL)
  3. washThe extract was washed with 200 mL portions of water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe resulting residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-ed2d610b24d049e99c1709642adafd07
Source dataset
uspto-grants-2004_06
Patent number
US06750364B2

Reaction notes

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