Water → HCID 90388236, compound

HRID 2201744Notes

Reaction equation

HRID 2201744 reaction equation
[CH3:1][C@:2]12[C@@:18]3(C[O:19]3)[CH2:17][CH2:16][C@@H:15]1[CH2:14][C@H:13]1[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:12]1[CH2:11][CH2:10][C@@H:9]([OH:21])[CH2:8]3)[CH2:3]2.C(N(CC)C(C)C)(C)C.[CH3:31][O:32][CH2:33]Cl.O>ClCCl>[CH3:31][O:32][CH2:33][O:21][C@H:9]1[CH2:8][C@H:7]2[C@@H:12]([C@@H:13]3[C@@H:4]([CH2:5][CH2:6]2)[CH2:3][C@@:2]2([CH3:1])[C:18](=[O:19])[CH2:17][CH2:16][C@@H:15]2[CH2:14]3)[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 90388631HCID 90388631, compound

Product 1

HCID 90388236HCID 90388236, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 46 (200 mg, 0.72 mmol) in dry dichloromethane (10 mL) was added N,N-diisopropylethylamine (260 mg, 2.0 mmol) and chloromethyl methyl ether (241 mg, 3.0 mmol) at room temperature. After 16 h, water (30 mL) was added and the product extracted into dichloromethane (50 mL×3). The combined extracts were dried, filtered and concentrated. The residue was purified by flash column chromatography (silica gel eluted with 10% EtOAc in hexanes) to give compound 47 (230 mg, 100%) as a white solid: [α]D25 −40.0 (c 0.20, CHCl3); 1H NMR (CDCl3) δ 4.60 (s, 2H), 3.83-3.82 (m, 1H), 3.31 (s, 3H), 0.81 (s, 3H); 13C NMR (CDCl3) δ 220.9, 94.5, 71.2, 55.0, 48.3, 47.7, 46.9, 45.6, 39.3, 38.1, 37.9, 36.6, 35.6, 33.9, 30.2, 28.3, 24.0, 2.39, 13.5; IR νmax 1740 cm−1.

Workup

  1. extractionthe product extracted into dichloromethane (50 mL×3)
  2. customThe combined extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (silica gel eluted with 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-850436dbbf0c43a697c9cf583723e3c9
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

Loading…