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Dibutyl sulfoxide → HCID 178455551, compound

HRID 272254
Notes
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Reaction equation

HRID 272254 reaction equation
[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][C:12]([O:13][CH2:14][C@@H:15]2[CH2:17][O:16]2)=[CH:11][C:10]=1[S:20]([CH2:22][CH2:23][CH2:24][CH3:25])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(S(CCCC)=O)CCC.S(C1C=CC([N+]([O-])=O)=CC=1)(OC[C@H]1OC1)(=O)=O.Cl.[NH2:54][C@H:55]1[CH2:60][CH2:59][C@H:58]([C:61]2[CH:75]=[CH:74][C:64]([O:65][C:66]([CH3:73])([CH3:72])[C:67]([O:69][CH2:70][CH3:71])=[O:68])=[CH:63][CH:62]=2)[CH2:57][CH2:56]1>C(O)C.CO>[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][C:12]([O:13][CH2:14][C@@H:15]([OH:16])[CH2:17][NH:54][C@H:55]2[CH2:60][CH2:59][C@H:58]([C:61]3[CH:62]=[CH:63][C:64]([O:65][C:66]([CH3:72])([CH3:73])[C:67]([O:69][CH2:70][CH3:71])=[O:68])=[CH:74][CH:75]=3)[CH2:57][CH2:56]2)=[CH:11][C:10]=1[S:20]([CH2:22][CH2:23][CH2:24][CH3:25])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 16568Dibutyl sulfoxideHCID 10868995(S)-(+)-Glycidyl-4-nitrobenzoateHCID 86604960(2S)-2-{[4-(benzyloxy)-3-(butylsulfinyl)phenoxy]methyl}oxiraneHCID 178471700HCID 178471700, compound

Product 1

HCID 178455551HCID 178455551, compound

Reagents, catalysts & solvents 2

HCID 702
Ethanol
Solvent
HCID 887MethanolSolvent

Procedure

A mixture of 0.742 g of (2S)-2-{[4-(benzyloxy)-3-(butylsulfinyl)phenoxy]methyl}oxirane (obtained by analogy with the method disclosed in WO 99/65895 but starting from the butyl sulfoxide instead of the methyl sulfoxide and using (S)-(+)-glycidyl nosylate; [α]D=+1.9 (c=1%, MeOH)) (2.06 mmol) and of 0.666 g of ethyl trans-2-[4-(4-aminocyclohexyl)phenoxy]-2,2-dimethylacetate hydrochloride (2.18 mmol) in ethanol (25 ml) is heated to reflux overnight. The solvent is evaporated under reduced pressure and the product obtained is purified by flash chromatography, elution being carried out with a methylene chloride/methanol/aqueous ammonia (95/5/0.5) mixture. The title product is obtained in the form of a yellow oil (0.730 g, 53%).

Workup

  1. customobtained by analogy with the method
  2. temperatureto reflux overnight
  3. customThe solvent is evaporated under reduced pressure
  4. customthe product obtained
  5. customis purified by flash chromatography, elution

Sources & evidence

ORD record
ord-0d6e40d8134f4804b9f665861cbf64a5
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07453010B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes