Benzyloxyacetyl chloride → N-Benzyloxyacetylmannosamine

HRID 1446029Notes

Reaction equation

HRID 1446029 reaction equation
C([O-])(O)=O.[Na+].Cl.[OH:7][CH:8]1[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:11]([OH:12])[C@@H:9]1[NH2:10].[CH2:19]([O:26][CH2:27][C:28](Cl)=[O:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:19]([O:26][CH2:27][C:28]([NH:10][C@H:9]1[C@@H:11]([OH:12])[C@H:13]([OH:14])[C@@H:15]([CH2:17][OH:18])[O:16][CH:8]1[OH:7])=[O:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 177085Benzyloxyacetyl chlorideHCID 516892Sodium BicarbonateHCID 9964480(3S,4R,5S,6R)-3-Amino-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol hydrochloride

Product 1

HCID 14160780N-BenzyloxyacetylmannosamineYield 68%

Procedure

To a round-bottom flask containing sat. NaHCO3 (9 mL) was added mannosamine hydrochloride (500 mg, 2.30 mmol). The solution was stirred for 1 h under N2, at which point benzyloxyacetyl chloride (0.44 mL, 2.8 mmol) was added dropwise via syringe. The biphasic mixture was stirred vigorously for 4 h resulting in a clear light yellow solution. The solution was concentrated and the residue was purified by silica gel chromatography eluting with a gradient of 20:1 to 10:1 CHCl3/MeOH to afford 512 mg (68%) of a viscous oil. IR (thin film): 3331, 2918, 2356, 1652, 1524 cm−1. 1H NMR (400 MHz, D2O): δ 3.26 (s, 1H), 3.33 (app t, 1H, J=6.7), 3.45 (app t, 1H, J=9.7), 3.54-3.66 (m, 1H), 3.69 (app d, 1H, J=4.8), 3.72 (d, 1H, J=2.0), 3.74-3.86 (m, 2H), 3.98 (dd, 1H, J=4.5, 9.8), 4.06 (s, 2H), 4.10 (s, 1H), 4.24-4.27 (m, 1H), 4.38-4.40 (m, 1H), 4.55 (s, 2H), 4.57 (d, 1H, J=4.3), 4.97 (s, 1H), 4.99 (s, 1H), 7.32-7.36 (m, 10H), 7.49 (d, 1H, J=10.7), 7.58 (d, 1H, J=9.6). 13C NMR (100 MHz, D2O): δ 52.9, 60.4, 66.8, 68.5, 68.7, 72.0, 73.5, 76.5, 89.3, 92.8, 128.5, 128.6, 128.7, 128.8. HRMS (FAB) m/z 328.1396 (MH+C15H22NO7 requires 328.1396).

Workup

  1. additionwas added dropwise via syringe
  2. customresulting in a clear light yellow solution
  3. concentrationThe solution was concentrated
  4. customthe residue was purified by silica gel chromatography
  5. washeluting with a gradient of 20:1 to 10:1 CHCl3/MeOH

Sources & evidence

ORD record
ord-7053fe6805934f489a194bd053fb062b
Source dataset
uspto-grants-2010_02
Patent number
US07667012B2

Reaction notes

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