Sodium Bicarbonate → HCID 67772265, compound

HRID 1808808Notes

Reaction equation

HRID 1808808 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([C@H:11]([NH:19][C:20](=O)OC(C)(C)C)[C:12]([N:14]2[CH2:17][CH:16]([OH:18])[CH2:15]2)=O)[CH2:10][CH2:9][CH2:8]1.C([O-])(O)=O.[Na+]>C1COCC1>[CH:7]1([C@H:11]([NH:19][CH3:20])[CH2:12][N:14]2[CH2:17][CH:16]([OH:18])[CH2:15]2)[CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 67772157HCID 67772157, compound

Product 1

HCID 67772265HCID 67772265, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1 M solution of LAH in THF (66.8 mL, 66.8 mmol) under nitrogen was heated to 45° C. A solution of (S)-tert-butyl 1-cyclobutyl-2-(3-hydroxyazetidin-1-yl)-2-oxoethylcarbamate (Compound Y2.1) (3.80 g, 13.4 mmol) in THF (20 mL) was added dropwise over 30 min. The resultant mixture was stirred at 47° C. over night. The mixture was cooled on an ice-bath and NaHCO3 (8% aq., 16 mL) was carefully added dropwise. The stirring was continued for 2 h at rt. The precipitate was filtered off and washed with DCM. The filtrate was concentrated and the residue dissolved in DCM and filtered through a 0.45 μm syringe filter. The filtrate was concentrated to give the title compound (2.23 g, 91%, 92% pure) as an oil. 1H NMR (400 MHz, CD3OD) δ 1.69-2.13 (6H), 2.2-2.38 (7H), 2.79 (1H), 2.89 (1H), 3.56-3.66 (2H), 4.26-4.34 (1H). Expected Number of protons: 20. OH- and NH-protons are exchanged with CD3OD.

Workup

  1. temperatureThe mixture was cooled on an ice-bath
  2. filtrationThe precipitate was filtered off
  3. washwashed with DCM
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe residue dissolved in DCM
  6. filtrationfiltered through a 0.45 μm syringe
  7. filtrationfilter
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b8949f5eb35d44fd8203e4b88f09f554
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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