Hydrochloric Acid → HCID 21107387, compound

HRID 1765538Notes

Reaction equation

HRID 1765538 reaction equation
[Cl:1]C1C=C(C=CC=1)C(OO)=O.[Cl:12][C:13]1[CH:32]=[CH:31][C:30](C=C)=[CH:29][C:14]=1[C:15]([NH:17][CH2:18][C:19]12[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]3)[CH2:20]1)[CH2:26]2)=[O:16].C[N:36]1[CH2:41][CH2:40][O:39]C[CH2:37]1.[OH-].[Na+].CN.Cl>ClCCl>[ClH:1].[Cl:12][C:13]1[CH:32]=[CH:31][C:30]([C@H:40]([OH:39])[CH2:41][NH:36][CH3:37])=[CH:29][C:14]=1[C:15]([NH:17][CH2:18][C:19]12[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]3)[CH2:20]1)[CH2:26]2)=[O:16]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 79724-MethylmorpholineHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acid2×HCID 21107411HCID 21107411, compound

Product 1

HCID 21107387HCID 21107387, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperoxybenzoic acid (mCPBA) (50%, 0.44 g) was added portionwise over 10 minutes to a solution of 2-chloro-5-ethenyl-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide (Example 9a)) (0.42 g)), (S,S)-[N,N′-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]manganese(III) chloride (44 mg) and N-methylmorpholine (0.74 g) in dichloromethane (10 mL) at −78° C. After stirring for 8 hours, a further portion of mCPBA (0.13 g) was added and the solution was left to warm slowly to room temperature over 16 hours. Sodium hydroxide (NaOH) (2M) was added, stirred for 1 hour and then methylamine (2M in methanol, 2 mL) was added. After stirring for 24 hours the reaction was concentrated, dichloromethane and water were added, the phases were separated and the aqueous was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate and concentrated. The resulting oil was purified by reverse phase HPLC (gradient 25–95% methanol in 1% aqueous trifluoroacetic acid). Further purification was performed by column chromatography (methanol/dichloromethane/ammonia (0.88) 1:20:0.5 to 15:100:0.5) gave an oil. Addition of excess 1M ethereal hydrogen chloride gave the titled compound as a white solid (158mg).

Workup

  1. waitthe solution was left
  2. stirringstirred for 1 hour
  3. stirringAfter stirring for 24 hours the reaction
  4. concentrationwas concentrated
  5. additiondichloromethane and water were added
  6. customthe phases were separated
  7. extractionthe aqueous was extracted with dichloromethane
  8. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customThe resulting oil was purified by reverse phase HPLC (gradient 25–95% methanol in 1% aqueous trifluoroacetic acid)
  11. customFurther purification
  12. customgave an oil

Sources & evidence

ORD record
ord-e7816cfa1a8246ecaaabb5ca6168af3f
Source dataset
uspto-grants-2007_06
Patent number
US07227038B2

Reaction notes

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