Tetrahydrofuran → HCID 21304103, compound

HRID 567374Notes

Reaction equation

HRID 567374 reaction equation
[C:1]([C:4]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:5]=1[C:6]1[C:7]([O:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:8][C:9]([CH2:24][O:25][CH2:26][CH:27]=[CH2:28])=[CH:10][C:11]=1[N:12]2[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:3])[NH2:2].[CH2:34]1COCC1>[Pt]=O>[C:1]([C:4]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:5]=1[C:6]1[C:7]([O:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:8][C:9]([CH2:24][O:25][CH2:26][CH2:27][CH3:28])=[CH:10][C:11]=1[N:12]2[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 10297262HCID 10297262, compound

Product 1

HCID 21304103HCID 21304103, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

Platinum oxide (30 mg) was added to a stirred THF (30 mL) solution containing the compound of Example 58 (120 mg, 0.262 mmol) under a nitrogen atmosphere. The mixture was then stirred under a hydrogen atmosphere for 30 minutes. After filtration and concentration, the residue was chromatographed on silica (gradient 0-6% methanol in methylene chloride) to afford the subtitled compound (117 mg, 97%) as a white solid. IR (KBr) 3364, 3166, 1758, 1742, 1642 cm−1; 1H-NMR (CDCl3): δ 0.91 (t, J=7.4 Hz, 3H, —CH3), 1.57-1.65 (m, 2H), 3.40 (t, J=6.6 Hz, 2H, —OCH2—), 3.83 (s, 3H, —OCH3), 4.60 (s, 2H, —OCH2—), 4.91 (s, 2H, —OCH2—), 5.52 (s, 2H, —NCH2—), 5.95 (br s, 1H, —NH), 6.06 (br s, 1H, —NH), 6.58 (s, 1H), 7.04 (s, 1H), 7.07-7.10 (m, 2H), 7.20-7.41 (m, 6H); ESIMS m/e 461 (M++1).

Workup

  1. filtrationAfter filtration and concentration
  2. customthe residue was chromatographed on silica (gradient 0-6% methanol in methylene chloride)

Sources & evidence

ORD record
ord-80c4ef39ebf4453ca504b39578c091ba
Source dataset
uspto-grants-2001_01
Patent number
US06177440B1

Reaction notes

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