Benzoyl chloride → HCID 66551752, compound

HRID 1422545Notes

Reaction equation

HRID 1422545 reaction equation
[NH2:1][C:2]1[S:3][C@H:4]2[O:10][C@H:9]([CH2:11][OH:12])[C@@H:8]([OH:13])[C@H:7]([OH:14])[C@H:5]2[N:6]=1.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1.C([O-])(O)=O.[Na+]>[OH:13][C@@H:8]1[C@@H:9]([CH2:11][OH:12])[O:10][C@H:4]2[C@H:5]([N:6]=[C:2]([NH:1][C:15](=[O:22])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:3]2)[C@H:7]1[OH:14]

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 67204778HCID 67204778, compound

Product 1

HCID 66551752HCID 66551752, compoundYield 24.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of (3aR,5R,6S,7R,7aR)-2-amino-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol (110 mg, 0.50 mmol) in THF (20 mL) and saturated aqueous NaHCO3 (5 mL) was treated with benzoyl chloride (77 mg, 0.55 mmol) for 1 hour at 0° C. After filtration, the solution was concentrated under vacuum to give a residue, which was purified by Prep-HPLC with the following conditions [(Agilent 1200 prep HPLC): Column, SunFire Prep C18,19*50 mm Sum; mobile phase, WATER with 0.03% NH4OH and CH3CN(10% CH3CN up to 45% in 10 min); Detector, UV 220 nm;] to give the title compound as a white solid (39.3 mg, 24%). (ES, m/z)[M+H]+324.9; 1H NMR (300 MHz, D2O) δ 7.83-7.85 (d, J=7.5 Hz, 2H), 7.49-7.54 (m, 1H), 7.36-7.42 (m, 2H), 6.13-6.15 (d, J=6.3 Hz, 1H), 3.97-4.02 (dd, J=6.3 Hz, 6.9 Hz, 1H), 3.89-3.93 (t, J=5.7 Hz, 1H), 3.45-3.73 (m, 4H).

Workup

  1. filtrationAfter filtration
  2. concentrationthe solution was concentrated under vacuum
  3. customto give a residue, which
  4. customwas purified by Prep-HPLC with the following conditions [(Agilent 1200 prep HPLC)

Sources & evidence

ORD record
ord-52b5da2c3859490fb0d4b3db444893c7
Source dataset
uspto-grants-2015_01
Patent number
US08927507B2

Reaction notes

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