Acetic Acid → (3aR,5R,6S,7R,7aR)-5-(hydroxymethyl)-2-(2-phenylmethoxyethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol

HRID 1396287Notes

Reaction equation

HRID 1396287 reaction equation
C([O:4][C@@H:5]1[C@@H:13]([CH2:14][O:15]C(=O)C)[O:12][C@H:11]2[C@H:7]([N:8]=[C:9]([NH:19][CH2:20][CH2:21][O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[S:10]2)[C@H:6]1[O:30]C(=O)C)(=O)C.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C.C(OCC)(=O)C>CO>[CH2:23]([O:22][CH2:21][CH2:20][NH:19][C:9]1[S:10][C@H:11]2[O:12][C@H:13]([CH2:14][OH:15])[C@@H:5]([OH:4])[C@H:6]([OH:30])[C@H:7]2[N:8]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 86701121[(3aR,5R,6S,7R,7aR)-6,7-diacetyloxy-2-(2-phenylmethoxyethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazol-5-yl]methyl acetate

Product 1

HCID 69082379(3aR,5R,6S,7R,7aR)-5-(hydroxymethyl)-2-(2-phenylmethoxyethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diolYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 129 (4.5 g, 9.4 mmol) in methanol (40 mL) was treated with potassium carbonate (260 mg, 2 mmol) for 3 hours at room temperature, then neutralized by the addition of acetic acid (0.5 mL). Volatiles were distilled out to give a residue, which was solidified from ethyl acetate. The solids were washed with ethyl acetate (3×20 mL) to give 130 as a light yellow solid (2.58 g, 80%). (ES, m/z) [M+H]+ 355.0; 1H NMR (300 MHz, D2O) δ 7.27-7.37 (m, 5H), 6.17 (d, J=6.3 Hz, 1H), 4.48 (s, 2H), 4.34-4.37 (m, 1H), 4.03-4.07 (m, 1H), 3.88-3.91 (m, 1H), 3.58-3.67 (m, 2H), 3.31-3.55 (m, 5H).

Workup

  1. distillationVolatiles were distilled out
  2. customto give a residue, which
  3. washThe solids were washed with ethyl acetate (3×20 mL)

Sources & evidence

ORD record
ord-4d0b7a12f8744fc08add0ec31cc451f1
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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