Hydrochloric Acid → 2-tert-butoxycarbonylamino-5-((S)-2-methoxymethyl-pyrrolidin-1-yl)-5-oxo-pentanoic acid

HRID 910404Notes

Reaction equation

HRID 910404 reaction equation
C[O:2][C:3](=[O:25])[CH:4]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:5][CH2:6][C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[CH2:14][O:15][CH3:16])=[O:8].[OH-].[Na+].Cl>CO>[C:21]([O:20][C:18]([NH:17][CH:4]([CH2:5][CH2:6][C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[CH2:14][O:15][CH3:16])=[O:8])[C:3]([OH:25])=[O:2])=[O:19])([CH3:22])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 673924162-tert-butoxycarbonylamino-5-((S)-2-methoxymethyl-pyrrolidin-1-yl)-5-oxo-pentanoic acid methyl ester

Product 1

HCID 673932042-tert-butoxycarbonylamino-5-((S)-2-methoxymethyl-pyrrolidin-1-yl)-5-oxo-pentanoic acidYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-tert-butoxycarbonylamino-5-((S)-2-methoxymethyl-pyrrolidin-1-yl)-5-oxo-pentanoic acid methyl ester (0.72 g, 2 mmol) in CH3OH (20 mL) was added 2 N aqueous sodium hydroxide (20 mL). After stirred at room temperature for 12 h, the mixture was acidified by the addition of 6 N aqueous hydrochloric acid at 0° C. to pH=4. Most of methanol was removed under reduced pressure and the residue was partitioned between CH2Cl2 (20 mL) and H2O (20 mL). The aqueous layer was further extracted with CH2Cl2 (20 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield the title compound (0.54 g, 79%) as a foamy solid which was used in the next step without further purification.

Workup

  1. customMost of methanol was removed under reduced pressure
  2. customthe residue was partitioned between CH2Cl2 (20 mL) and H2O (20 mL)
  3. extractionThe aqueous layer was further extracted with CH2Cl2 (20 mL)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-59049b7c5eb74afdb4747b9d3ea303e6
Source dataset
uspto-grants-2011_09
Patent number
US08022096B2

Reaction notes

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