Triethylamine → HCID 69084851, compound

HRID 1396229Notes

Reaction equation

HRID 1396229 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1[S:4][C@H:5]2[O:11][C@H:10]([CH2:12][OH:13])[C@@H:9]([OH:14])[C@H:8]([OH:15])[C@H:6]2[N:7]=1.C(N(CC)CC)C.[C:24]([Si:28](Cl)([CH3:30])[CH3:29])([CH3:27])([CH3:26])[CH3:25]>CN(C1C=CN=CC=1)C.CN(C=O)C>[Si:28]([O:13][CH2:12][C@H:10]1[O:11][C@H:5]2[C@H:6]([N:7]=[C:3]([N:2]([CH3:16])[CH3:1])[S:4]2)[C@@H:8]([OH:15])[C@@H:9]1[OH:14])([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:30])[CH3:29]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 10848161HCID 10848161, compound

Product 1

HCID 69084851HCID 69084851, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol (1 g, 4.03 mmol), DMAP (49.2 mg, 0.40 mmol) and triethylamine (611 mg, 6.05 mmol) in DMF (50 mL) was added tert-butylchlorodimethylsilane (665 mg, 4.43 mmol). After stirred overnight at 50° C., the resulting mixture was concentrated under vacuum to provide a residue, which was purified by silica gel column, eluted with 2-5% MeOH in dichloromethane to give compound 8 as a yellow solid (1.0 g, 65%). (ES, m/z): [M+H]+ 263.0; 1H NMR (300 MHz, CDCl3) δ 6.33-6.35 (d, J=6.3 Hz, 1H), 4.35-4.39 (t, J=5.7 Hz, 1H), 4.18-4.21 (t, J=4.5 Hz, 1H), 3.81-3.84 (m, 3H), 3.62-3.67 (m, 1H), 3.05 (s, 6H), 0.93 (s, 9H), 0.11 (s, 6H).

Workup

  1. concentrationthe resulting mixture was concentrated under vacuum
  2. customto provide a residue, which
  3. customwas purified by silica gel column
  4. washeluted with 2-5% MeOH in dichloromethane

Sources & evidence

ORD record
ord-79b8e038bc854c8796c1bee452b40788
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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