Triethylamine → HCID 86701107, compound

HRID 1396256Notes

Reaction equation

HRID 1396256 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][F: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:25]([Si:29](Cl)([CH3:31])[CH3:30])([CH3:28])([CH3:27])[CH3:26].C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[Si:29]([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][F: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:25]([CH3:28])([CH3:27])[CH3:26])([CH3:31])[CH3:30]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 86701108HCID 86701108, compound

Product 1

HCID 86701107HCID 86701107, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 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(2-fluoroethyl)carbamate (16 g, 43.7 mmol) in dichloromethane (100 mL) was added tert-butylchlorodimethylsilane (7.6 g, 50.7 mmol), 4-dimethylaminopyridine (530 mg, 4.34 mmol) and triethylamine (6.6 g, 65 mmol). After stirred for 6 h at room temperature, the resulting mixture was concentrated under vacuum to give a residue, which was purified by a silica gel column, eluting with 20% petroleum in ethyl acetate to give compound 69 as pale yellow oil (10 g, 48%). (ES, m/z) [M+H]+ 481.0; 1H NMR (300 MHz, CDCl3) δ 6.17-6.19 (d, J=6.3 Hz, 1H), 4.42-4.74 (m, 3H), 3.52-4.26 (m, 7H), 1.56 (s, 9H), 0.92 (s, 9H), 0.10 (s, 6H).

Workup

  1. concentrationthe resulting mixture was concentrated under vacuum
  2. customto give a residue, which
  3. customwas purified by a silica gel column
  4. washeluting with 20% petroleum in ethyl acetate

Sources & evidence

ORD record
ord-a387d277897e46eca6a333a159902df1
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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