Hydrochloric Acid → HCID 59049305, compound

HRID 1264475Notes

Reaction equation

HRID 1264475 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:8][CH2:7][N:6]1[C:9](=[O:18])[C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:4].CCOCC.[Li+].[OH-].Cl>O.CO>[O:18]=[C:9]([N:6]1[CH2:7][CH2:8][C@H:5]1[C:3]([OH:4])=[O:2])[C:10](=[O:17])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 3939Lithium HydroxideHCID 59049303HCID 59049303, compound

Product 1

HCID 59049305HCID 59049305, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (2S)-methyl-1-(1,2-dioxo-2-phenylethyl)azetidine-2-carboxylate from Reference Example 9 (522.5 mg; 2.11 mmol) in a 1:1 mixture of ether:methanol (20.0 mL) was added 1N LiOH in water (3.9 mL) at about 0° C. The mixture was stirred under argon at about 0° C. for about 30 minutes and then at about room temperature overnight. The pH was adjusted to about pH 1 by adding 1N HCl and then the mixture was diluted with water and extracted with dichloromethane. The organic layers were then washed with brine, dried over sodium sulfate and concentrated to give 415.2 mg (67% yield) of the product as a yellow solid. 1H NMR (CDCl3) δ 2.33-2.91 (series of m, 2H); 4.08-4.51 (series of m, 2H); 5.09 and 5.31 (dd, 1H, J=10.3, 6.9, J=10.3, 6.9); 7.40-7.73 (m, 3H); 8.04-8.19 (m, 2H); 8.25-8.80 (br, 1H).

Workup

  1. customat about room temperature
  2. customovernight
  3. extractionextracted with dichloromethane
  4. washThe organic layers were then washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2140c862d8ba4029b8ee83f5eb4662ba
Source dataset
uspto-grants-2003_04
Patent number
US06544976B1

Reaction notes

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