Methanol → HCID 69084319, compound

HRID 1396275Notes

Reaction equation

HRID 1396275 reaction equation
C([O:8][C@@H:9]1[C@@H:17]([CH2:18][CH:19]([F:21])[F:20])[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:22]([CH3:24])[CH3:23])[S:14]2)[C@H:10]1[O:25]CC1C=CC=CC=1)C1C=CC=CC=1.B(Cl)(Cl)Cl.CO.[NH4+].[OH-]>ClCCl>[F:21][CH:19]([F:20])[CH2:18][C@H:17]1[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:22]([CH3:24])[CH3:23])[S:14]2)[C@@H:10]([OH:25])[C@@H:9]1[OH:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 25135Boron TrichlorideHCID 69084459HCID 69084459, compound

Product 1

HCID 69084319HCID 69084319, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 109 (270 mg, 0.6 mmol) in dichloromethane (20 mL) was treated with BCl3 (6 mL, 6 mmol, 1M in dichloromethane) for 2 hours at −60° C., then the reaction was quenched with methanol (20 mL). Volatiles were distilled out under vacuum to give a residue, which was dissolved into methanol (5 mL) and neutralized by Con. NH4OH (2 ml, 26% aqueous solution). After concentration, the crude product was purified by a silica gel column, eluted with 10% methanol in dichloromethane to give the title compound as a white solid (41 mg, 25%); (ES, m/z) [M+H]+ 283.0; 1HNMR (300 MHz, D2O) δ 6.17 (d, J=6.3 Hz, 1H), 5.77-6.14 (m, 1H), 4.12 (t, J=6.0 Hz, 1H), 3.93 (t, J=5.1 Hz, 1H), 3.68-3.73 (m, 1H), 3.43-3.48 (m, 1H), 2.91 (s, 6H), 1.99-2.35 (m, 2H).

Workup

  1. customthe reaction was quenched with methanol (20 mL)
  2. distillationVolatiles were distilled out under vacuum
  3. customto give a residue, which
  4. concentrationAfter concentration
  5. customthe crude product was purified by a silica gel column
  6. washeluted with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-e16601295d14432bb69c381e5f3964fa
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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