Methanol → HCID 69082735, compound

HRID 1396274Notes

Reaction equation

HRID 1396274 reaction equation
C([O:8][C@@H:9]1[C@@H:17]([CH2:18][CH2:19][F:20])[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:21]([CH3:23])[CH3:22])[S:14]2)[C@H:10]1[O:24]CC1C=CC=CC=1)C1C=CC=CC=1.B(Cl)(Cl)Cl.CO.[NH4+].[OH-]>ClCCl>[CH3:23][N:21]([CH3:22])[C:13]1[S:14][C@H:15]2[O:16][C@H:17]([CH2:18][CH2:19][F:20])[C@@H:9]([OH:8])[C@H:10]([OH:24])[C@H:11]2[N:12]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 25135Boron TrichlorideHCID 69085766HCID 69085766, compound

Product 1

HCID 69082735HCID 69082735, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 108 (300 mg, 0.7 mmol) in dichloromethane (20 mL) was treated with BCl3 (7 mL, 7 mmol, 1 M in dichloromethane) for 2 hours at −60° C., then quenched by the addition of methanol (10 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 (35 mg, 20%); (ES, m/z) [M+H]+ 265.0; 1HNMR (300 MHz, D2O) δ 6.16 (d, J=6.3 Hz, 1H), 4.60 (t, J=4.8 Hz, 1H), 4.45 (t, J=4.8 Hz, 1H), 4.10 (t, J=6.0 Hz, 1H), 3.92 (t, J=4.8 Hz, 1H), 3.62-3.66 (m, 1H), 3.42-3.60 (m, 1H), 2.90 (s, 6H), 2.06-2.20 (m, 1H), 1.67-1.88 (m, 1H).

Workup

  1. customquenched by the addition of methanol (10 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-69ab9555c82c47b089653319796d7360
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

Loading…