Triethylamine → HCID 70563215, compound

HRID 971405Notes

Reaction equation

HRID 971405 reaction equation
[C:1]([CH:5]1[O:11][CH:10]2[CH:7]([C:8](=[O:26])[N:9]2[C:12](=[C:23]([CH3:25])[CH3:24])[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[NH:6]1)([O:3][CH3:4])=[O:2].C(N(CC)CC)C.[C:34]1([CH2:40][S:41](Cl)(=[O:43])=[O:42])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O1CCCC1>[C:1]([CH:5]1[O:11][CH:10]2[CH:7]([C:8](=[O:26])[N:9]2[C:12](=[C:23]([CH3:24])[CH3:25])[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14])[N:6]1[S:41]([CH2:40][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=[O:43])=[O:42])([O:3][CH3:4])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74740Phenylmethanesulfonyl chlorideHCID 13019671HCID 13019671, compound

Product 1

HCID 70563215HCID 70563215, compoundYield 105.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 500 mg of benzyl α-(3ξ-carbomethoxy-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate in 10 ml of tetrahydrofuran are added 0.27 ml of triethylamine and 343 mg of phenylmethanesulfonyl chloride under ice-cooling in nitrogen atmosphere, and the mixture stirred for 25 minutes. The reaction mixture is poured into ice water and extracted with ethyl acetate, and the extract washed with water, dried on sodium sulfate and concentrated under reduced pressure to yield 756 mg of benzyl α-(3ξ-carbomethoxy-2-phenylmethanesulfonyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate.

Workup

  1. temperaturecooling in nitrogen atmosphere
  2. extractionextracted with ethyl acetate
  3. washthe extract washed with water
  4. customdried on sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-faa8dbc0a86e4ee1bb262a0a27dcaaa5
Source dataset
uspto-grants-1979_07
Patent number
US04159984

Reaction notes

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