Water → HCID 70504214, compound

HRID 1155423Notes

Reaction equation

HRID 1155423 reaction equation
P(O[C:18]([CH3:48])=[C:19]([N:33]1[C:39](=[O:40])[CH:38]2[CH:34]1[S:35][C:36]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[N:37]2)[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)=[O:21])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.[NH:49]1[CH2:54][CH2:53][O:52][CH2:51][CH2:50]1.O>C(#N)C>[CH2:41]([C:36]1[S:35][CH:34]2[CH:38]([C:39](=[O:40])[N:33]2[C:19](=[C:18]([N:49]2[CH2:54][CH2:53][O:52][CH2:51][CH2:50]2)[CH3:48])[C:20]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=2)=[O:21])[N:37]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 54246939HCID 54246939, compound

Product 1

HCID 70504214HCID 70504214, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of diphenyl 1-(3-benzyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl)-1-(p-nitrobenzyloxycarbonyl)-prop-1-en-2-yl phosphate (6.86 g) in acetonitrile (50 ml) at 0°-5° C. was added morpholine (1.83 ml) dropwise and the reaction mixture stirred at this temperature for 2 hours. Water (50 ml) was added and the mixture was extracted with ethyl acetate (40 ml). The organic layer was separated, washed with water (30 ml) and saturated sodium chloride solution (30 ml), dried with magnesium sulphate, filtered and evaporated to give the title compound as a yellow foam in almost quantitative yield. The product obtained was a mixture of geometric isomers (ca. 1:1.4) about the enamine double bond and was identical to that produced in Example 6.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (40 ml)
  2. customThe organic layer was separated
  3. washwashed with water (30 ml) and saturated sodium chloride solution (30 ml)
  4. dry with materialdried with magnesium sulphate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-5363b5112c1145e58f65fea8fe8c5a40
Source dataset
uspto-grants-1981_11
Patent number
US04301280

Reaction notes

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