Sodium Hydroxide → (S)-3-Boc-2,2-dimethyloxazolidine-4-propanoic Acid

HRID 218407Notes

Reaction equation

HRID 218407 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:22])[CH2:6][CH2:7][C@H:8]1[CH2:12][O:11][C:10]([CH3:14])([CH3:13])[N:9]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>>[C:18]([O:17][C:15]([N:9]1[C@@H:8]([CH2:7][CH2:6][C:5]([OH:22])=[O:4])[CH2:12][O:11][C:10]1([CH3:14])[CH3:13])=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 15930243Methyl (S)-3-Boc-2,2-dimethyloxazolidine-4-propanoate

Product 1

HCID 10635974(S)-3-Boc-2,2-dimethyloxazolidine-4-propanoic AcidYield 91%

Conditions

Temperature
23 °C

Procedure

An aqueous solution of sodium hydroxide (195 mL, 4.0 M in H2O, 0.261 mol, 3.0 eq) was added to a solution of (S)-tert-butyl 4-(3-methoxy-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate (25.1 g, 0.087 mol), and the resulting cloudy reaction mixture was stirred at 23° C. for 3.5 hr. The mixture was concentrated under reduced pressure to ˜50 mL volume and then was partitioned between 0.5 M HCl (360 ml) and EtOAc (2×360 ml). The combined organic layers were dried over Na2SO4 and were filtered. The filtrate was concentrated under reduced pressure to give (S)-3-(3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl)propanoic acid (21.6 g, 91%), which was used without further purification.

Workup

  1. customthe resulting cloudy reaction mixture
  2. concentrationThe mixture was concentrated under reduced pressure to ˜50 mL volume
  3. customwas partitioned between 0.5 M HCl (360 ml) and EtOAc (2×360 ml)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationwere filtered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3b15f65b02c049d38d8913ee61929b9e
Source dataset
uspto-grants-2012_06
Patent number
US08198453B2

Reaction notes

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