Hydrochloric Acid → HCID 86749750, compound

HRID 1078718Notes

Reaction equation

HRID 1078718 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([O:13][Si](C(C)(C)C)(C)C)[CH2:10][C@H:9]1[C:21](=[O:27])[CH2:22][C:23](=[O:26])[NH:24][CH3:25])=O)(C)(C)C.[ClH:28]>CO>[ClH:28].[OH:13][C@H:11]1[CH2:12][NH:8][C@H:9]([C:21](=[O:27])[CH2:22][C:23](=[O:26])[NH:24][CH3:25])[CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22865011HCID 22865011, compound

Product 1

HCID 86749750HCID 86749750, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[2-(N-methylcarbamoyl)-1-oxoethyl]pyrrolidine (2.07 g, 5.3 mmol) in methanol (10 ml) was added a 5.5N hydrogen chloride--methanol solution (6 ml, 33 mmol). The mixture was stirred at room temperature for 6 h. The reaction solution was concentrated in vacuo. Tetrahydrofuran and ethanol were added to the obtained residue, and the precipitate was collected by filtration and washed with ethanol to obtain (2S,4R)-4-hydroxy-2-[2-(N-methylcarbamoyl)-1-oxoethyl]pyrrolidine monohydrochloride (737 mg, yield: 62%).

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. additionTetrahydrofuran and ethanol were added to the obtained residue
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-67a4d905d8a94c0ea3c6fe07db6b2ca8
Source dataset
uspto-grants-1996_08
Patent number
US05550121

Reaction notes

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