Tetrahydrofuran → HCID 87611431, compound

HRID 1829714Notes

Reaction equation

HRID 1829714 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:33][CH:34]=C)[CH2:10][N:11]([CH2:26][CH2:27][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])[CH:15]=2)=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8].C1C[O:39]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:39])[CH2:10][N:11]([CH2:26][CH2:27][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])[CH:15]=2)=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 24477Sodium ThiosulfateHCID 68883041HCID 68883041, compound

Product 1

HCID 87611431HCID 87611431, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

To a stirred slurry of N-[2-(3,4-dichlorophenyl)-4-pentenyl]-N-[(2-carboxyethyl)ethyl]-3-cyano-1-naphthamide (0.56 g) and NaIO4 (0.82 g) in 60 mL 1:1 THF:H2O was slowly added 0.55 mL OsO4 solution (4% w/w in H2O). Mixture was stired 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 0.26 g of N-[2-(3,4-dichlorophenyl)-4-oxobutyl]-N-[(2-carboxyethyl)ethyl]-3-cyano-1-naphtharide after purification by chromatography (5:4:1 Hexane:DCM:EtOAc); MS: m/z 511 (M+); 1H NMR (CDCl3) δ 9.79 (s), 9.56 (s), 9.55 (s), 8.26-8.19 (m), 8.00-7.82 (m), 7.79-7.20 (m), 7.00-6.90 (m), 6.81-6.72 (m), 6.68-6.55 (m), 4.45 (t), 4.30-2.78 (m), 2.60-2.25 (m), 1.40-1.12 (m).

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 0.26 g of N-[2-(3,4-dichlorophenyl)-4-oxobutyl]-N-[(2-carboxyethyl)ethyl]-3-cyano-1-naphtharide after purification by chromatography (5:4:1 Hexane:DCM:EtOAc)

Sources & evidence

ORD record
ord-9ad4dc0c1ae744839ca5b40945c51b98
Source dataset
uspto-grants-2006_06
Patent number
US07064136B2

Reaction notes

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