Triethylamine → HCID 69280761, compound

HRID 1396241Notes

Reaction equation

HRID 1396241 reaction equation
[OH:1][C@@H:2]1[C@@H:10]([CH2:11][OH:12])[O:9][C@H:8]2[C@H:4]([N:5]=[C:6]([N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[S:7]2)[C@H:3]1[OH:22].C(N(CC)CC)C.[C:30]([Si:34](Cl)([CH3:36])[CH3:35])([CH3:33])([CH3:32])[CH3:31]>CN(C1C=CN=CC=1)C.ClCCl>[Si:34]([O:12][CH2:11][C@H:10]1[O:9][C@H:8]2[C@H:4]([N:5]=[C:6]([N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:19])[CH3:17])[S:7]2)[C@@H:3]([OH:22])[C@@H:2]1[OH:1])([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:36])[CH3:35]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 69280759HCID 69280759, compound

Product 1

HCID 69280761HCID 69280761, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl (3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(methyl)carbamate (30 g, 90 mmol), DMAP (550 mg, 4.5 mmol) and triethylamine (18.2 g, 180 mmol) in dichloromethane (200 mL) was added tert-butylchlorodimethylsilane (16.3 g, 108 mmol) at 0° C. The resulting solution was stirred for 4 h at room temperature, and then concentrated under vacuum to provide a residue, which was purified by silica gel column, eluted with 1% methanol in dichloromethane to give compound 26 as a white solid (20 g, 50%). (ES, m/z): [M+H]+ 449.0; 1H NMR (300 MHz, CDCl3) δ 6.10-6.12 (d, J=6.9 Hz, 1H), 4.15-4.24 (m, 2H), 3.83-3.97 (m, 5H), 3.60 (m, 1H), 2.58-2.66 (m, 2H), 1.55 (s, 9H), 1.18 (m, 3H), 0.91 (s, 9H), 0.09 (s,

Workup

  1. concentrationconcentrated under vacuum
  2. customto provide a residue, which
  3. customwas purified by silica gel column
  4. washeluted with 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-ca17617f4ffe44abbaa8d8d272f9c49d
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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