Water → HCID 18442426, compound

HRID 458938Notes

Reaction equation

HRID 458938 reaction equation
[CH2:1]([C:5]1([CH2:28][CH2:29][CH2:30][CH3:31])[C:11](=[O:12])[N:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[C:9]2[CH:22]=[CH:23][C:24]([O:26][CH3:27])=[CH:25][C:8]=2[S:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].C(Cl)Cl.C([O-])([O-])=[O:36].[K+].[K+].ClC1C=C(C=CC=1)C(OO)=O.[OH2:52]>>[O:52]=[S:7]1(=[O:36])[C:8]2[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:9]=2[N:10]([C:13]2[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=2)[C:11](=[O:12])[C:5]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:6]1

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 18442489HCID 18442489, compound

Product 1

HCID 18442426HCID 18442426, compoundYield 87%

Conditions

Temperature
0 °C

Procedure

To 3,3-dibutyl-4-oxo-5-(4-nitrophenyl)-8-methoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 103; 2.57 g, 5.8 mmol) was added DCM (130 ml), water (130 ml) and K2CO3 (2.44 g, 17.6 mmol). The reaction mixture was cooled down to 0° C. and m-chloroperoxybenzoic acid (3.42 g, 13.9 mmol) was added in one portion. The reaction was allowed to complete overnight with the temperature slowly rising to room temperature. Then NaHCO3aq (sat) was added and the two layers were separated. The water layer was then extracted three times with DCM. The combined organic layers was dried, filtered and evaporated under reduced pressure. The product was purified by flash chromatography using DCM as eluent to give the title compound 2.4 g (87%). M/z 475.4.

Workup

  1. customslowly rising to room temperature
  2. additionThen NaHCO3aq (sat) was added
  3. customthe two layers were separated
  4. extractionThe water layer was then extracted three times with DCM
  5. customThe combined organic layers was dried
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-df4e84ca1dce4fa78fe482a400f74d5c
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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