Ethanol → HCID 69084129, compound

HRID 1396253Notes

Reaction equation

HRID 1396253 reaction equation
[CH3:1][N:2]([CH3:35])[C:3]1[S:4][C@H:5]2[O:11][C@H:10]([C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[C@H:8]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[C@H:6]2[N:7]=1.C(N(S(F)(F)F)CC)C.C(O)C>ClCCl>[CH3:35][N:2]([CH3:1])[C:3]1[S:4][C@H:5]2[O:11][C@H:10]([C@@H:12]([OH:14])[CH3:13])[C@@H:9]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=3)[C@H:8]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[C@H:6]2[N:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 123472(Diethylamino)sulfur trifluorideHCID 69082386HCID 69082386, compound

Product 1

HCID 69084129HCID 69084129, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-((3aR,5S,6S,7R,7aR)-2-(dimethylamino)-6,7-bis(4-methoxybenzyloxy)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)ethanone (280 mg, 0.56 mmol) in dichloromethane (10 mL) was treated with (diethylamino)sulfur trifluoride (451 g, 2.80 mol) and ethanol (5.2 mg, 0.11 mmol) overnight at room temperature. The reaction was then quenched by addition of sat. aqueous sodium carbonate solution (50 mL), and extracted with dichloromethane (3×20 mL). The combined organic layers were dried over anhydrous magnesium sulfate and condensed under vacuum to give a crude product 55 (140 mg), which was used in the next step without further purification. (ES, m/z) [M+H]+ 523.0; 1H NMR (300 MHz, CD3Cl) δ 1H NMR (300 MHz, CDCl3) δ 7.24-7.30 (m, 4H), 6.84-6.95 (m, 4H), 6.30-6.32 (m, 1H), 4.57-4.62 (m, 4H), 4.27-4.35 (m, 2H), 3.81-3.91 (m, 8H), 2.99-3.01 (m, 6H), 1.56-1.62 (m, 3H).

Workup

  1. customThe reaction was then quenched by addition of sat. aqueous sodium carbonate solution (50 mL)
  2. extractionextracted with dichloromethane (3×20 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate and condensed under vacuum

Sources & evidence

ORD record
ord-306451c94cac44a8b557df95bf37fbb2
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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