Triethylamine → HCID 86701096, compound

HRID 1396235Notes

Reaction equation

HRID 1396235 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]([CH2:21][CH2:22][CH3:23])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[S:7]2)[C@H:3]1[OH:24].C(N(CC)CC)C.[C:32]([Si:36](Cl)([CH3:38])[CH3:37])([CH3:35])([CH3:34])[CH3:33]>CN(C1C=CN=CC=1)C.ClCCl>[Si:36]([O:12][CH2:11][C@H:10]1[O:9][C@H:8]2[C@H:4]([N:5]=[C:6]([N:13]([CH2:21][CH2:22][CH3:23])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:17])[CH3:18])[S:7]2)[C@@H:3]([OH:24])[C@@H:2]1[OH:1])([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:38])[CH3:37]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 69280760HCID 69280760, compound

Product 1

HCID 86701096HCID 86701096, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution 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(propyl)carbamate (45 g, 124 mmol), DMAP (760 mg, 6 mmol) and triethylamine (25.1 g, 248 mmol) in dichloromethane (300 mL) was added tert-butylchlorodimethylsilane (22.4 g, 149 mmol). After stirred for 6 h at room temperature, the mixture was condensed to provide a residue, which was purified by silica gel column, eluted with 10-30% ethyl acetate in petroleum ether to give compound 17 as a yellow oil (43 g. 65%). (ES, m/z): [M+H]+ 477.1; 1H NMR (300 MHz, CDCl3) δ 6.12-6.14 (d, J=6.3 Hz, 1H), 4.40-4.45 (m, 1H), 3.84-3.96 (m, 4H), 3.64-3.71 (m, 1H), 3.13-3.30 (m, 3H), 1.67-1.74 (m, 2H), 1.53 (s, 9H), 0.93-0.98 (m, 3H), 0.92 (s, 9H), 0.12 (s, 6H).

Workup

  1. customcondensed
  2. customto provide a residue, which
  3. customwas purified by silica gel column
  4. washeluted with 10-30% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-47e95bed02ad4841afb5cc415936fea7
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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