Ethyl isocyanate → HCID 86715425, compound

HRID 1422547Notes

Reaction equation

HRID 1422547 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.[N:15]([CH2:18][CH3:19])=[C:16]=[O:17]>CN(C)C=O>[OH:13][CH: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:16]([NH:15][CH2:18][CH3:19])=[O:17])[S:3]2)[C@H:7]1[OH:14]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 67204778HCID 67204778, compound

Product 1

HCID 86715425HCID 86715425, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 (100 mg, 0.45 mmol) in N,N-dimethylformamide (10 mL) was treated with isocyanatoethane (32 mg, 0.45 mmol) for 1 hour at room temperature. The reaction mixture was condensed to give a residue, which was purified by Prep-HPLC with the following conditions [(Prep-HPLC): Column, 19*150 mm; mobile phase, water with 0.03% NH3H2O and CH3CN (10% CH3CN up to 45% in 10 min); Detector, 220 nm] to give the title compound as a white solid (20 mg, 15%). (ES, m/z)[M+H]+291.9; 1H NMR (300 MHz, D2O) δ6.51-6.52 (d, J=6.3 Hz, 1H), 4.60-4.65 (m, 1H), 3.96-4.02 (t, J=9.0 Hz, 1H), 3.67-3.78 (m, 3H), 3.43-3.49 (t, J=9.6 Hz, 1H), 3.08-3.18 (m, 2H), 0.98-1.02 (t, J=7.2 Hz, 3H).

Workup

  1. customcondensed
  2. customto give a residue, which
  3. customwas purified by Prep-HPLC with the following conditions [(Prep-HPLC)

Sources & evidence

ORD record
ord-41162a586eec47768f715cf0adabe8e7
Source dataset
uspto-grants-2015_01
Patent number
US08927507B2

Reaction notes

Loading…