Sodium → rel-1,1-Dimethylethyl N-[(2R,3S)-2-methyl-4-oxo-3-azetidinyl]carbamate

HRID 371216Notes

Reaction equation

HRID 371216 reaction equation
[Na].[C:2]([O:6][C:7]([NH:9][C@H:10]1[C@@H:13]([CH3:14])[N:12](OC)[C:11]1=[O:17])=[O:8])([CH3:5])([CH3:4])[CH3:3]>N.O1CCCC1>[C:2]([O:6][C:7]([NH:9][C@H:10]1[C@@H:13]([CH3:14])[NH:12][C:11]1=[O:17])=[O:8])([CH3:5])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 5360545SodiumHCID 57291996Carbamic acid, (1-methoxy-2-methyl-4-oxo-3-azetidinyl)-, 1,1-dimethylethyl ester, (2R-cis)-

Product 1

HCID 57285608rel-1,1-Dimethylethyl N-[(2R,3S)-2-methyl-4-oxo-3-azetidinyl]carbamateYield 94.4%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium (1.35 g) is dissolved in about 300 ml of liquid ammonia at -50° C. and 5.87 g of (3S-cis)-3-t-Butoxycarbonylamino-1-methoxy-4-methylazetidinone in 35 ml tetrahydrofuran is added dropwise via syringe. An additional 10 ml of tetrahydrofuran is used for rinsing. Near the end of the addition about 100 mg of additional sodium is added. The mixture is stirred for five more minutes, then quenched by adding 3.35 g of solid ammonium chloride in one portion. Ammonia is blown off with a nitrogen stream and 250 ml of ethyl acetate is added to the residue. After filtration and washing the solid with ethyl acetate, the combined filtrate is stripped of solvent to give 4.82 g of the title compound.

Workup

  1. washfor rinsing
  2. additionNear the end of the addition about 100 mg of additional sodium
  3. additionis added
  4. customquenched
  5. additionby adding 3.35 g of solid ammonium chloride in one portion
  6. additionis added to the residue
  7. filtrationAfter filtration
  8. washwashing the solid with ethyl acetate

Sources & evidence

ORD record
ord-796d948365914944b96eb7295abccb2f
Source dataset
uspto-grants-1985_07
Patent number
US04529698

Reaction notes

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