Tetrahydrofuran → HCID 22054689, compound

HRID 1829719Notes

Reaction equation

HRID 1829719 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:33][CH2:34]C=CCCC)[CH2:10][N:11]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:12]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[C:16]([C:24]#[N:25])[C:15]=2[CH2:26][CH3:27])=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8].C1C[O:43]CC1.[O-]S([O-])(=S)=O.[Na+].[Na+]>O=[Os](=O)(=O)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:33][CH:34]=[O:43])[CH2:10][N:11]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:12]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[C:16]([C:24]#[N:25])[C:15]=2[CH2:26][CH3:27])=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 24477Sodium ThiosulfateHCID 68883160HCID 68883160, compound

Product 1

HCID 22054689HCID 22054689, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

To a stirred slurry of N-[2-(3,4-dichlorophenyl)-4-pentenylbutyl]-N-[(carboxymethyl)methyl]-3-cyano-2-ethyl-1-naphthamide (0.51 g) and NaIO4 (0.47 g) in 100 mL 1:1 THF:H2O was slowly added 0.32 mL OsO4 solution (4% w/w in H2O). Mixture was stirred for 18 h, 10 mL sat'd Na2S2O3(aq) was added, THF was evaporated, and aqueous residue was extracted with DCM. Extracts were dried over Na2SO4, filtered, and concentrated. This gave 0.64 g of N-[2-(3,4-dichlorophenyl)-4-oxobutyl]-N-[(carboxymethyl)methyl]-3-cyano-1-naphthamide after purification by chromatography (100:1, DCM:MeOH); MS: m/z 511 (M+); 1H NMR (CDCl3) δ 9.53 (s), 8.25 (s), 7.79 (d), 7.70-7.20 (m), 6.89 (d), 6.73 (d), 6.48 (dd), 4.58-4.20 (m), 3.88 (s), 3.84 (s), 3.60-3.21 (m), 3.18-2.82 (m), 2.65-2.32 (m), 1.33 (t).

Workup

  1. additionwas added
  2. customTHF was evaporated
  3. extractionaqueous residue was extracted with DCM
  4. dry with materialExtracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThis gave 0.64 g of N-[2-(3,4-dichlorophenyl)-4-oxobutyl]-N-[(carboxymethyl)methyl]-3-cyano-1-naphthamide after purification by chromatography (100:1, DCM:MeOH)

Sources & evidence

ORD record
ord-b3c9383f303b494a9540381a215255ec
Source dataset
uspto-grants-2006_06
Patent number
US07064136B2

Reaction notes

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