Diisopropylethylamine → HCID 71164616, compound

HRID 1182288Notes

Reaction equation

HRID 1182288 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(N(CC)C(C)C)(C)C.[C:50](=O)([O:73]C1C=CC([N+]([O-])=O)=CC=1)[O:51][C@H:52]([CH2:57][N:58]1[CH:62]=[CH:61][C:60]([C:63]2[CH:68]=[CH:67][C:66]([C:69]([F:72])([F:71])[F:70])=[CH:65][CH:64]=2)=[N:59]1)[C:53]([CH3:56])([CH3:55])[CH3:54]>CN(C)C=O.C(OCC)(=O)C>[OH:16][C@H:4]([C@@H:3]([NH:2][C:50](=[O:73])[O:51][C@H:52]([CH2:57][N:58]1[CH:62]=[CH:61][C:60]([C:63]2[CH:64]=[CH:65][C:66]([C:69]([F:70])([F:71])[F:72])=[CH:67][CH:68]=2)=[N:59]1)[C:53]([CH3:56])([CH3:55])[CH3:54])[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

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 69512678HCID 69512678, compoundHCID 69512755HCID 69512755, compoundHCID 69512874HCID 69512874, compound

Product 1

HCID 71164616HCID 71164616, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 90 mg (0.21 mmol) of N-[(2S,3S)-3-amino-2-hydroxyheptyl]-2-pyridinesulfonamide hydrochloride & N-[(2R,3S)-3-amino-2-hydroxyheptyl]-2-pyridinesulfonamide hydrochloride and 83 mg (0.63 mmol) of N,N-diisopropylethylamine in 2 mL N,N-dimethylformamide was added 102 mg (0.21 mmol) of (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl 4-nitrophenyl carbonate. The reaction mixture was stirred at room temperature for 48 h. It was diluted with ethyl acetate, washed with one portion of 1M sodium hydroxide and with 1 portion of brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with ethyl acetate:hexanes (3:1) to afford 90 mg (68%) of (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S)-1-{(1S)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate & (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S)-1-{(1R)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate. 1H-NMR (300 MHz, DMSO-d6): δ 8.70 (d, J=4 Hz, 1H), 8.11–7.45 (m, 10H), 6.76 (s, 1H), 6.54 (d, J=9 Hz, 1H), 4.90–4.76 (m, 2H), 4.46 (d, J=13 Hz, 1H), 4.16 (m, 1H), 3.05 (m, 1H), 1.27 (m, 1H), 1.05–0.86 (m, 14H), 0.68 (m, 3H); ES-LCMS m/z 648 (M+Na).

Workup

  1. washwashed with one portion of 1M sodium hydroxide and with 1 portion of brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with ethyl acetate:hexanes (3:1)

Sources & evidence

ORD record
ord-771eaf9917f94fd68d3c2e0baf32e22c
Source dataset
uspto-grants-2007_10
Patent number
US07288541B2

Reaction notes

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