m-Chloroperbenzoic acid → HCID 21517662, compound

HRID 1283694Notes

Reaction equation

HRID 1283694 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][CH:13]([N:21]1[CH:24]([S:25][CH2:26][C:27]#[C:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:23]([NH:36][C:37]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:22]1=[O:56])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>C(O)C>[Cl:12][CH:13]([N:21]1[CH:24]([S:25]([CH2:26][C:27]#[C:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:9])[CH:23]([NH:36][C:37]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:22]1=[O:56])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21517645HCID 21517645, compound

Product 1

HCID 21517662HCID 21517662, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Conditions

Temperature
0 °C

Procedure

m-Chloroperbenzoic acid (30mg) in ethanol-free chloroform (3ml) was added in 10 minutes to a stirred solution of 1-(1-chloro-1-t-butoxycarbonylmethyl)-4-(4-phenylbut-2-ynylthio)-3-(triphenylmethylamino)azetidin-2-one (99mg) in ethanol-free chloroform (3ml) at 0°C. The mixture was stirred for a further 30 minutes at 0°C. The reaction mixture was diluted with ethanol-free chloroform (10ml) and washed successively with saturated sodium bicarbonate solution (5ml) and brine (2 × 5ml). The dried (MgSO4) organic layer was evaporated to give a gum which upon re-evaporation from dry ether gave 1-(1-chloro-1-tert-butoxycarbonylmethyl)-4-(4-phenylbut-2-ynylsulphinyl)-3-triphenylmethylamino-azetidin-2-one as a solid foam (92mg, 91%)

Workup

  1. washwashed successively with saturated sodium bicarbonate solution (5ml) and brine (2 × 5ml)
  2. dry with materialThe dried (MgSO4) organic layer
  3. customwas evaporated
  4. customto give a gum which
  5. customupon re-evaporation from dry ether

Sources & evidence

ORD record
ord-8614301d3172477986d9d0cf5e21ae38
Source dataset
uspto-grants-1976_08
Patent number
US03975383

Reaction notes

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