Piperidine → HCID 21517657, compound

HRID 1283333Notes

Reaction equation

HRID 1283333 reaction equation
[C:1]([O:5][C:6]([C:8]([N:28]1[CH:31]([S:32][CH2:33][C:34]#[C:35][C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)[CH:30]([NH:43][C:44]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:29]1=[O:63])=[P:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1CCCCC1.C(OCC)(=[O:72])C>>[C:1]([O:5][C:6]([C:8]([N:28]1[CH:31]([S:32][CH2:33][C:34](=[O:72])[CH2:35][C:36]2[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=2)[CH:30]([NH:43][C:44]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)[C:29]1=[O:63])=[P:9]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 8082PiperidineHCID 8857Ethyl AcetateHCID 53811313HCID 53811313, compound

Product 1

HCID 21517657HCID 21517657, compound

Procedure

1-(1-t-Butoxycarbonyl-1-triphenylphosphoranylidenemethyl)-3-(triphenylmethylamino)-4-(3-p-fluorophenylprop-2-ynylthio)azetidin-2-one (370mg) was refluxed is piperidine (25ml) under nitrogen for 6 hours. The mixture was cooled, diluted with ethyl acetate and the organic layer washed with N-hydrochloric acid and brine, dried and evaporated to an amorphous solid. Chromatography on silica gave 1-(1-t-butoxycarbonyl-1-triphenylphosphoranylidenemethyl)-3-(triphenylmethylamino)-4-(3-p-fluorophenyl-2-oxopropylthio)azetidin-2-one as an amorphous solid (330mg).

Workup

  1. customfor 6 hours
  2. temperatureThe mixture was cooled
  3. washthe organic layer washed with N-hydrochloric acid and brine
  4. customdried
  5. customevaporated to an amorphous solid

Sources & evidence

ORD record
ord-2d859024c6804d7e98c17a26fc298cd3
Source dataset
uspto-grants-1976_08
Patent number
US03974154

Reaction notes

Loading…