Hydrochloric Acid → HCID 54131553, compound

HRID 279812Notes

Reaction equation

HRID 279812 reaction equation
C([Li])(CC)C.[CH3:6][C:7]([CH3:18])([O:9][C:10]([NH:12][C@H:13]1[CH2:16][NH:15][C:14]1=[O:17])=[O:11])[CH3:8].[CH3:19][S:20]([N:23]=[C:24]=[S:25])(=[O:22])=[O:21].P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl>O1CCCC1.O.C(OCC)(=O)C>[CH3:8][C:7]([CH3:18])([O:9][C:10]([NH:12][C@H:13]1[CH2:16][N:15]([C:24](=[S:25])[NH:23][S:20]([CH3:19])(=[O:22])=[O:21])[C:14]1=[O:17])=[O:11])[CH3:6]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 62657Potassium Phosphate, TribasicHCID 11116749Tert-butyl N-[(3S)-2-oxoazetidin-3-yl]carbamateHCID 12297546Methanesulfonyl isothiocyanateHCID 178418400CID 53628100

Product 1

HCID 54131553HCID 54131553, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sec-Butyl lithium (9.25 ml of 1.35 M solution in cyclohexane) was added to a stirred solution of (S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxoazetidine (2.33 g) in 250 ml of dry tetrahydrofuran at -75° C. under nitrogen. After stirring for 2 minutes, (methylsulfonyl)-isothiocyanate (1.75 ml) was added, and the solution was stirred for 25 minutes at -75° C. and poured into 125 ml of 0.5 M pH 5.5 monobasic potassium phosphate buffer. Ethyl acetate and water were added, and the pH was adjusted to 2.5 (3N hydrochloric acid). The ethyl acetate layer was washed with water, dried with sodium sulfate, and evaporated to a residue (3.69 g), which was recrystallized from ethyl acetate to give 2.04 g of the title compound. Recrystallization of a portion from ethyl acetate gave crystals, melting point 181° C.,dec.

Workup

  1. stirringthe solution was stirred for 25 minutes at -75° C.
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried with sodium sulfate
  4. customevaporated to a residue (3.69 g), which
  5. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1f2eec29ea224c8ab5172b390e8221df
Source dataset
uspto-grants-1986_05
Patent number
US04587047

Reaction notes

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