Hydrochloric Acid → (2S,3R)-2-{[(tert-butoxy)carbonyl]amino}-3-[(tert-butyldimethylsilyl)oxy]butanoic acid

HRID 1056115Notes

Reaction equation

HRID 1056115 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@H:14]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH3:15])[C:10]([O:12]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>C1COCC1.[Cl-].[Na+].O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@H:14]([O:16][Si:17]([C:20]([CH3:21])([CH3:23])[CH3:22])([CH3:18])[CH3:19])[CH3:15])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 11824217(2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)butanoate

Product 1

HCID 13273792(2S,3R)-2-{[(tert-butoxy)carbonyl]amino}-3-[(tert-butyldimethylsilyl)oxy]butanoic acidYield 100.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of (2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)butanoate (614a) (1.07 g, 3.08 mmol) in THF (25 mL) was treated with 1.0 M aq. LiOH (6.16 mL, 6.16 mmol) and the mixture was stirred for 72 h. The mixture was diluted with saturated aq. brine (100 mL) containing 1.0 M aq. HCl (10 mL), and extracted into EtOAc (2×100 mL). The combined organic extracts were dried (MgSO4) and concentrated to give (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)butanoic acid (614b) (1.03 g, 3.09 mmol, 100% yield) as a viscous colorless oil that crystallized upon standing. LC-MS m/z 356.1, [M+Na]+.

Workup

  1. extractionextracted into EtOAc (2×100 mL)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-defa9febd3be444db588990eb4ed46e9
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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