Water → HCID 13631270, compound

HRID 279803Notes

Reaction equation

HRID 279803 reaction equation
C([NH+](CC)CC)C.[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]([N:21]2[CH2:24][C@H:23]([NH2:25])[C:22]2=[O:26])=[O:20])(=[O:17])=[O:16])=[CH:11][CH:10]=1.C(N(CC)CC)C.[C:34]1([CH2:40][C:41](Cl)=[O:42])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.O>C(#N)C>[CH3:8][C:9]1[CH:10]=[CH:11][C:12]([S:15]([NH:18][C:19]([N:21]2[CH2:24][C@H:23]([NH:25][C:41](=[O:42])[CH2:40][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:22]2=[O:26])=[O:20])(=[O:17])=[O:16])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 131714658HCID 131714658, compound

Product 1

HCID 13631270HCID 13631270, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(S)-1-[[[(4-Methylphenyl)sulfonyl]amino]-carbonyl]-2oxo-3-aminoazetidine, triethylammonium salt (626 mg, see example 2) was dissolved in dry acetonitrile (25 ml) and stirred under nitrogen in an ice bath. Triethylamine (0.57 ml) was added, followed by phenylacetyl chloride (0.324 ml). After 3 hours an equal volume of water was added, the pH was adjusted to 7.5, and the acetonitrile was removed in vacuo. The aqueous residue was extracted twice with ethyl acetate to remove neutral material. The aqueous layer was then acidified to pH 2.0 and extracted three times with ethyl acetate. The acidic extract was dried over anhydrous sodium sulfate and evaporated to dryness in vacuo, yielding 544 mg. This crude product, and an additional 481 mg of crude product from two other runs were combined and purified by chromatography on a column of SilicAR CC-4 (100 g), using dichloromethane and dichloromethane:methanol, 99:1 as eluants. The amorphous product was crystallized from acetonitrile to give 154 mg of crystalline material, melting point 170°-172° C.

Workup

  1. customthe acetonitrile was removed in vacuo
  2. extractionThe aqueous residue was extracted twice with ethyl acetate
  3. customto remove neutral material
  4. extractionextracted three times with ethyl acetate
  5. extractionThe acidic extract
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customevaporated to dryness in vacuo
  8. customyielding 544 mg
  9. custompurified by chromatography on a column of SilicAR CC-4 (100 g)
  10. customThe amorphous product was crystallized from acetonitrile

Sources & evidence

ORD record
ord-dfeb3700c0e7472f9dabe1adb9bc73fc
Source dataset
uspto-grants-1986_05
Patent number
US04587047

Reaction notes

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