Methanol → HCID 69082944, compound

HRID 1396277Notes

Reaction equation

HRID 1396277 reaction equation
C([O:8][C@@H:9]1[C@@H:17]([CH2:18][C:19]([F:22])([F:21])[F:20])[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:23]([CH3:25])[CH3:24])[S:14]2)[C@H:10]1[O:26]CC1C=CC=CC=1)C1C=CC=CC=1.B(Cl)(Cl)Cl.CO.[NH4+].[OH-]>ClCCl>[CH3:25][N:23]([CH3:24])[C:13]1[S:14][C@H:15]2[O:16][C@H:17]([CH2:18][C:19]([F:22])([F:20])[F:21])[C@@H:9]([OH:8])[C@H:10]([OH:26])[C@H:11]2[N:12]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 25135Boron TrichlorideHCID 69093575HCID 69093575, compound

Product 1

HCID 69082944HCID 69082944, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound 112 (300 mg, 0.6 mmol) in dichloromethane (10 mL) was added BCl3 (3 mL, 3 mmol, 1M in dichloromethane) at −78° C. The resulting solution was kept at −20° C. for 1 hour, 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 (94.2 mg, 49%). (ES, m/z): [M+H]+ 300.9; 1H NMR (D2O, 300 MHz) δ 6.16 (d, J=6.3 Hz, 1H), 4.11-4.15 (m, 1H), 3.93-3.97 (m, 1H), 3.77-3.83 (m, 1H), 3.44-3.48 (m, 1H), 2.91 (s, 6H), 2.52-2.68 (m, 1H), 2.37-2.49 (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-255cc33ed2be433fb00bc7660500f236
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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