Potassium Carbonate → HCID 21970483, compound

HRID 1637424Notes

Reaction equation

HRID 1637424 reaction equation
[N:1]([C@H:4]1[C@H:16]([O:17]C(=O)C)[C@H:15]([O:21]C(=O)C)[C@H:14]([CH3:25])[O:13][CH:5]1[S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+:2]=[N-:3].C([O-])([O-])=O.[K+].[K+]>CO>[N:1]([C@H:4]1[C@H:16]([OH:17])[C@H:15]([OH:21])[C@H:14]([CH3:25])[O:13][CH:5]1[S:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 21970485HCID 21970485, compound

Product 1

HCID 21970483HCID 21970483, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 22 (4.40 g, 12.1 mmol) in 120 mL of methanol is added K2CO3 (5.97 g, 36.2 mmol). The reaction mixture is stirred at room temperature for 1.5 h and then neutralized with amberlite resin, filtered, concentrated and purified by flash chromatography (5% methanol/CH2Cl2) to yield 3.10 g (91%, 2 steps) of phenyl 2-azido-2,6-dideoxy-1-thio-L-galactopyranoside (23) as a 2.5:1 (α:β) mixture of anomers: Rf 0.10 (25% EtOAc/petroleum ether); 1H NMR (CDCl3, 270 MHz) mixture of anomers, δ 7.61-7.27 (m, 10H), 5.61 (d, J=5.3 Hz, 1H, H-1α), 4.50 (q, J=6.6 Hz, 1H, H-5α), 4.42 (d, J=9.9 Hz, 1H, H-1β), 4.11 (dd, J=10.1, 5.4 Hz, 2H, H-3α,β), 3.88-3.85 (m, 3H), 3.73 (br s, 1H), 3.63 (q, J=6.3 Hz, 1H, H-5β), 3.59-3.40 (m, 1H), 2.81 (br s, 1H, OH), 2.47 (br s, 1H, OH), 2.23 (br s, 1H, OH), 1.72 (br s, 1H, OH), 1.37 (d, J=6.3 Hz, 3H, H-6β), 1.30 (d, J=6.6 Hz, 3H, H-6α).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. custompurified by flash chromatography (5% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-651707775e99444483296702867b5cc9
Source dataset
uspto-grants-2000_03
Patent number
US06040433

Reaction notes

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