p-Toluenesulfonic acid monohydrate → HCID 59454115, compound

HRID 1662056Notes

Reaction equation

HRID 1662056 reaction equation
C(OC([NH:8][C@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)=[O:15])=O)(C)(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[NH2:8][C@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)=[O:15]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrate2×HCID 59454018HCID 59454018, compound

Product 1

HCID 59454115HCID 59454115, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 4-methoxybenzyl (1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylate (2.2 g) and methanol (11 ml) was added p-toluene sulfonic acid hydrate (1.2 g) at room temperature, followed by stirring at 40° C. for 13 hours. Further, p-toluene sulfonic acid hydrate (0.24 g) was added thereto, followed by stirring at 40° C. for 3 hours. The reaction mixture was concentrated under reduced pressure, and 1 M hydrochloric acid and diethyl ether were added to the residue. The aqueous layer was separated, and the organic layer was extracted with 1 M hydrochloric acid. The aqueous layer was combined, and sodium hydrogen carbonate was added thereto under ice-cooling to adjust the pH to about 7. The reaction mixture was extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 4-methoxybenzyl (1R,2S)-2-aminocyclopentanecarboxylate (1.1 g).

Workup

  1. stirringby stirring at 40° C. for 3 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and 1 M hydrochloric acid and diethyl ether
  3. additionwere added to the residue
  4. customThe aqueous layer was separated
  5. extractionthe organic layer was extracted with 1 M hydrochloric acid
  6. additionsodium hydrogen carbonate was added
  7. temperatureunder ice-cooling
  8. extractionThe reaction mixture was extracted with ethyl acetate
  9. washwashed with saturated brine
  10. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4628f56af7d84f9ba5f86c12e0f03775
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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