Diisopropylethylamine → HCID 58981745, compound

HRID 1182312Notes

Reaction equation

HRID 1182312 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:17][CH2:18][CH2:19][CH3:20])[C@@H:4]([OH:16])[CH2:5][NH:6][S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)(=[O:9])=[O:8].Cl.N[C@@H](CCCC)[C@H](O)CNS(C1C=CC=CN=1)(=O)=O.[C:41](=O)([O:60]C1C=CC([N+]([O-])=O)=CC=1)[O:42][C@H:43]([CH2:48][N:49]1[C:53]2[CH:54]=[C:55]([Cl:59])[C:56]([Cl:58])=[CH:57][C:52]=2[N:51]=[CH:50]1)[C:44]([CH3:47])([CH3:46])[CH3:45].C(N(C(C)C)CC)(C)C>CN(C)C=O>[OH:16][C@@H:4]([C@@H:3]([NH:2][C:41](=[O:60])[O:42][C@H:43]([CH2:48][N:49]1[C:53]2[CH:54]=[C:55]([Cl:59])[C:56]([Cl:58])=[CH:57][C:52]=2[N:51]=[CH:50]1)[C:44]([CH3:47])([CH3:46])[CH3:45])[CH2:17][CH2:18][CH2:19][CH3:20])[CH2:5][NH:6][S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)(=[O:9])=[O:8]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 58981729HCID 58981729, compoundHCID 69512755HCID 69512755, compoundHCID 69512874HCID 69512874, compound

Product 1

HCID 58981745HCID 58981745, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

73 mg (0.18 mmol) of N-[(2S,3S)-3-amino-2-hydroxyheptyl]-2-pyridinesulfonamide hydrochloride & N-[(2R,3S)-3-amino-2-hydroxyheptyl]-2-pyridinesulfonamide hydrochloride was slurried in 3.5 mL of anhydrous dimethylformamide. Addition of 80 mg (0.18 mmol) of (1S)-1-[(5,6-dichloro-1H-benzimidazol-1-yl)methyl]-2,2-dimethylpropyl 4-nitrophenyl carbonate followed by 0.14 mL (0.72 mmol) of diisopropylethylamine resulted in a light yellow solution, which was stirred for 3 d. It was then concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate, and the solution was washed with a saturated aqueous sodium bicarbonate solution., dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography eluting with a methanol:chloroform solution (1:9) to afford 54 mg (50%) of (1 S)-1-[(5,6-dichloro-1H-benzimidazol-1-yl)methyl]-2,2-dimethylpropyl (1S)-1-{(1R)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate & (1S)-1-[(5,6-dichloro-1H-benzimidazol-1-yl)methyl]-2,2-dimethylpropyl (1S)-1-{(1S)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate. ES-LCMS n/z 622 (M+Na) retention time=3.96 min.

Workup

  1. customresulted in a light yellow solution, which
  2. concentrationIt was then concentrated under reduced pressure
  3. dissolutionThe resulting residue was dissolved in ethyl acetate
  4. washthe solution was washed with a saturated aqueous sodium bicarbonate solution
  5. dry with material, dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with a methanol

Sources & evidence

ORD record
ord-db62519e690d403496cdcfe75b2e5752
Source dataset
uspto-grants-2007_10
Patent number
US07288541B2

Reaction notes

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