Pyridine-2-sulfonyl Chloride → HCID 86596687, compound

HRID 1182286Notes

Reaction equation

HRID 1182286 reaction equation
[NH2:1][CH2:2][C@@H:3]([C@@H:5]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][CH2:7][CH2:8][CH3:9])[OH:4].NC[C@H]([C@@H](NC(=O)OC(C)(C)C)CCCC)O.[N:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[S:41](Cl)(=[O:43])=[O:42]>ClCCl.C(=O)(O)[O-].[Na+]>[OH:4][CH:3]([C@@H:5]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][NH:1][S:41]([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][N:35]=1)(=[O:43])=[O:42]

Participants

6

Reactant 3

HCID 3787675Pyridine-2-sulfonyl ChlorideHCID 58981684HCID 58981684, compoundHCID 58981744HCID 58981744, compound

Product 1

HCID 86596687HCID 86596687, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a biphasic mixture of 4.93 g (20 mmol) of tert-butyl (1S)-1-[(1S)-2-amino-1-hydroxyethyl]pentylcarbamate & tert-butyl (1S)-1-[(1R)-2-amino-1-hydroxyethyl]pentylcarbamate in 32 mL dichloromethane and 15 mL saturated sodium bicarbonate was added 24 mL (24 mmol) of 1 M 2-pyridinesulfonyl chloride in dichloromethane. The reaction mixture was stirred overnight and then extracted with dichloromethane. The extract was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with ethyl acetate:hexanes (6:4) to afford 5.00 g (65%) of tert-butyl (1S)-1-{(1SR)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate & tert-butyl (1S)-1-{(1R)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate. 1H-NMR (300 MHz, DMSO-d6): δ 8.73 (d, J=4 Hz, 1H), 8.09 (t, J=8 Hz, 1H), 7.93 (dd, J=8 Hz, J=4 Hz, 1H), 7.68 (m, 1H), 7.60 and 7.54 ((t, J=6 Hz), (t, J=6 Hz), 1H), 6.55 and 6.36 ((d, J=9 Hz), (d, J=9 Hz), 1H), 4.78 (m, 1H), 3.50–2.70 (m, 4H), 1.61 (m, 1H), 1.37-1.05 (m, 14H), 0.86 (t, J=7 Hz, 3H); ES-LCMS m/z 410 (M+Na).

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with ethyl acetate:hexanes (6:4)

Sources & evidence

ORD record
ord-159ecb11e6dd48d0af61471d114c5737
Source dataset
uspto-grants-2007_10
Patent number
US07288541B2

Reaction notes

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