Water → HCID 70469116, compound

HRID 279784Notes

Reaction equation

HRID 279784 reaction equation
[N+](=CC([C@@H]1N(CC2C=CC(OC)=CC=2OC)[C:8](=[O:21])[C@H]1CC)=O)=[N-].CO[C:26]([C@H:28]1[C@H:31]([CH2:32][CH3:33])[C:30](=[O:34])[N:29]1[CH2:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][C:37]=1[O:44][CH3:45])=O.[OH2:46]>>[CH3:45][O:44][C:37]1[CH:38]=[C:39]([O:42][CH3:43])[CH:40]=[CH:41][C:36]=1[CH2:35][N:29]1[C:30](=[O:34])[C@@H:31]([CH2:32][CH3:33])[C@@H:28]1[CH2:26][C:8]([OH:21])=[O:46]

Participants

4

Reactant 3

HCID 962WaterHCID 86740767HCID 86740767, compoundHCID 86740769HCID 86740769, compound

Product 1

HCID 70469116HCID 70469116, compoundYield 47.1%

Procedure

2.93 g (10 millimole) of trans-4-diazoacetyl-1-(2,4-dimethoxy-benzyl)-3-ethyl-2-azetidinone-which may contain some methyl-trans-1-(2,4-dimethoxy-benzyl)-3-ethyl-4-oxo-2-azetidine-carboxylate too--are dissolved in 100 ml of peroxide-free tetrahydrofuran and to the solution 50 ml of water are added. The solution is irradiated with a high pressure mercury vapor lamp (HPK) under argon in a pyrex apparatus equipped with a submersed lamp for about 4 hours (until the diazoacetyl derivative is converted). From the solution the tetrahydrofuran is evaporated in vacuo, the residue is diluted with water to 150 ml and made alkaline by adding 4 ml of a 10% aqueous sodium hydroxide solution. The alkaline solution is extracted three times with 30 ml of dichloromethane each and the aqueous phase is acidified with concentrated hydrochloride acid to pH 2. The acidic solution is extracted three times with 30 ml of dichloro methane each. The organic phase is dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated to dryness. On rubbing with ether the residue becomes crystalline. Thus 1.44 g of the desired compound are obtained, yield: 47.1%. M.p.: 131° C.

Workup

  1. additionare added
  2. customThe solution is irradiated with a high pressure mercury vapor lamp (HPK) under argon in a pyrex apparatus
  3. customFrom the solution the tetrahydrofuran is evaporated in vacuo
  4. additionthe residue is diluted with water to 150 ml
  5. additionby adding 4 ml of a 10% aqueous sodium hydroxide solution
  6. extractionThe alkaline solution is extracted three times with 30 ml of dichloromethane each and the aqueous phase
  7. extractionThe acidic solution is extracted three times with 30 ml of dichloro methane each
  8. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-460feb90a0754f39bd5e5c50a44ac720
Source dataset
uspto-grants-1986_05
Patent number
US04587049

Reaction notes

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