Diisopropylethylamine → HCID 58981737, compound

HRID 1182318Notes

Reaction equation

HRID 1182318 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].N[C@@H](CCCC)[C@H](O)CNS(C1C=CC=CN=1)(=O)=O.[C:40](=O)([O:60]C1C=CC([N+]([O-])=O)=CC=1)[O:41][C@H:42]([CH2:47][O:48][C:49]1[CH:54]=[CH:53][C:52]([N:55]2[CH:59]=[CH:58][N:57]=[CH:56]2)=[CH:51][CH:50]=1)[C:43]([CH3:46])([CH3:45])[CH3:44].C(N(CC)C(C)C)(C)C>CN(C)C=O>[OH:16][C@H:4]([C@@H:3]([NH:2][C:40](=[O:60])[O:41][C@H:42]([CH2:47][O:48][C:49]1[CH:54]=[CH:53][C:52]([N:55]2[CH:59]=[CH:58][N:57]=[CH:56]2)=[CH:51][CH:50]=1)[C:43]([CH3:45])([CH3:46])[CH3:44])[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 58981708HCID 58981708, compoundHCID 58981743HCID 58981743, compoundHCID 69512874HCID 69512874, compound

Product 1

HCID 58981737HCID 58981737, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 154 mg (0.31 mmol) of N-[(2S,3S)-3-amino-2-hydroxyheptyl]-2-pyridinesulfonamide hydrochloride & N-[(2R,3S)-3-amino-2-hydroxyheptyl]-2-pyridinesulfonamide in 3 mL of dimethylformamide, 132 mg (0.31 mmol) of (1S)-1-{[4-(1H-imidazol-1-yl)phenoxy]methyl}-2,2-dimethylpropyl 4-nitrophenyl carbonate was added, followed by 0.25 mL (1.43 mmol) of N,N-diisopropylethylamine. The reaction mixture was stirred for 18 h at room temperature. It was concentrated, a saturated sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel column chromatography eluting with an methanol:chloroform solution (1:9) to yield 101.3 mg (57%) of (1S)-1-{[4-(1H-imidazol-1-yl)phenoxy]methyl}-2,2-dimethylpropyl (1S)-1-{(1S)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate and (1S)-1-{[4-(1H-imidazol-1-yl)phenoxy]methyl}-2,2-dimethylpropyl (1S)-1-{(1R)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate. ES-LCMS m/z 574 (M+H) Rt=2.7 min.

Workup

  1. concentrationIt was concentrated
  2. additiona saturated sodium bicarbonate solution was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with an methanol

Sources & evidence

ORD record
ord-34e6bb4447ae43b580cf286949cbbef0
Source dataset
uspto-grants-2007_10
Patent number
US07288541B2

Reaction notes

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