Tetrahydrofuran → HCID 69082734, compound

HRID 1396244Notes

Reaction equation

HRID 1396244 reaction equation
CC([O-])(C)C.[K+].[CH3:7][N:8]([CH3:40])[C:9]1[S:10][C@H:11]2[O:17][C@H:16]([CH:18]=O)[C@@H:15]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[C@H:14]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)[C@H:12]2[N:13]=1.C1[CH2:45][O:44][CH2:43]C1>>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][O:20][C@@H:15]2[C@@H:16](/[CH:18]=[CH:43]/[O:44][CH3:45])[O:17][C@H:11]3[C@H:12]([N:13]=[C:9]([N:8]([CH3:40])[CH3:7])[S:10]3)[C@H:14]2[O:30][CH2:31][C:32]2[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 86701093HCID 86701093, compound

Product 1

HCID 69082734HCID 69082734, compoundYield 14%

Conditions

Temperature
0 °C

Procedure

A solution of Ph3PCH2OCH3Br (2.0 g, 5.90 mmol) in THF (30 mL) was treated with t-BuOK (645 mg, 5.76 mmol) at −10° C. for 30 min, and followed by addition of (3aR,5S,6S,7R,7aR)-2-(dimethylamino)-6,7-bis(4-methoxybenzyloxy)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-5-carbaldehyde (700 mg, 1.37 mmol). After stirred for 3 h at 0° C., the resulting solution was quenched with ice-water (20 mL), and extracted with ethyl acetate (2×20 mL). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated to give a residue, which was purified by a silica gel column, eluted with 10-50% ethyl acetate in petroleum ether to give the product 37 as a yellow oil (100 mg, 14%). (ES, m/z) [M+H]+ 515.0; 1H NMR (300 MHz, CDCl3) δ 7.15-7.35 (m, 4H), 6.84-6.98 (m, 4H), 6.45 (d, J=7.8 Hz, 1H), 6.28 (d, J=6.3 Hz, 1H), 5.21 (m, 1H), 4.45-4.89 (m, 4H), 4.18 (t, J=5.7 Hz, 1H), 3.94 (t, J=4.8 Hz, 1H), 3.87-3.91 (m, 1H), 3.78 (s, 6H), 3.56-3.65 (m, 1H), 3.52 (s, 3H), 2.92 (s, 6H).

Workup

  1. customthe resulting solution was quenched with ice-water (20 mL)
  2. extractionextracted with ethyl acetate (2×20 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give a residue, which
  6. customwas purified by a silica gel column
  7. washeluted with 10-50% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-7f1a265935af4072b0ec3bc43f921d5f
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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