Potassium Carbonate → HCID 69082892, compound

HRID 1425674Notes

Reaction equation

HRID 1425674 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]([N:19]3[CH2:22][CH2:21][CH2:20]3)[S:10]2)[C@H:6]1[O:23]C(=O)C)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[N:19]1([C:9]2[S:10][C@H:11]3[O:12][C@H:13]([CH2:14][OH:15])[C@@H:5]([OH:4])[C@H:6]([OH:23])[C@H:7]3[N:8]=2)[CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 69280858HCID 69280858, compound

Product 1

HCID 69082892HCID 69082892, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3aR,5R,6S,7R,7aR)-5-(acetoxymethyl)-2-(azetidin-1-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl diacetate (360 mg, 0.93 mmol) in methanol (5 mL) was treated with potassium carbonate (13 mg, 0.09 mmol) overnight at 40° C. The reaction mixture was concentrated under vacuum to give a residue, which was purified by Prep-HPLC with the following conditions [(Agilent 1200 prep HPLC): Column, X-Bridge C18, 19*50 mm 3.5 um; mobile phase, Water with 0.05% NH4OH and CH3CN (3% CH3CN up to 9% in 5 min; Detector, UV 220 nm)] to give compound 3 as a white solid (100 mg, 40%). (ES, m/z) [M+H]+ 261.0; 1H NMR (300 MHz, DMSO+D2O) δ 6.25-6.27 (d, J=6.3 Hz, 1H), 3.92-3.96 (t, J=5.7 Hz, 1H), 3.83-3.88 (m, 4H), 3.68-3.71 (t, J=4.8 Hz, 1H), 3.55-3.58 (m, 1H), 3.25-3.42 (m, 3H), 2.21-2.26 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customto give a residue, which
  3. customwas purified by Prep-HPLC with the following conditions [(Agilent 1200 prep HPLC)

Sources & evidence

ORD record
ord-216605097b0c4b8d923491bcc352656f
Source dataset
uspto-grants-2015_01
Patent number
US08933040B2

Reaction notes

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