Hydrochloric Acid → HCID 57633911, compound

HRID 1772083Notes

Reaction equation

HRID 1772083 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:17](=[O:23])[N:18]([CH2:21]C)CC)=[C:9]([CH:16]=1)CNC(=O)OC)([CH3:4])([CH3:3])[CH3:2].O1CCCC1.[OH-].[Li+].Cl>CO>[C:1]([C:5]1[CH:16]=[C:9]2[C:8](=[CH:7][CH:6]=1)[C:17](=[O:23])[NH:18][CH2:21]2)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86697934HCID 86697934, compound

Product 1

HCID 57633911HCID 57633911, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

A 25-mL microwave vial equipped with a magnetic stirrer was charged with 103b (858 mg, 2.68 mmol), tetrahydrofuran (5 mL), methanol (5 mL) and 2 M aqueous lithium hydroxide (5 mL). The vial was loaded in a Biotage microwave and heated at 110° C. for 2.5 h. After this time, the solution was neutralized with 2 M hydrochloric acid to pH 7 and concentrated in vacuo. The resulting residue was partitioned between ethyl acetate (150 mL) and water (30 mL). The aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine (30 mL), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica, 50% ethyl acetate to 100% ethyl acetate/hexanes) to afford a 56% yield (285 mg) of 103c as an off-white solid: mp=132-134° C.; 1H NMR (300 MHz, CDCl3) δ 7.80 (d, 1H, J=7.8 Hz), 7.52 (m, 2H), 6.71 (br s, 1H), 4.44 (s, 2H), 1.37 (s, 9H), MS (ESI+) m/z 190.1 (M+H).

Workup

  1. customA 25-mL microwave vial equipped with a magnetic stirrer
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was partitioned between ethyl acetate (150 mL) and water (30 mL)
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×20 mL)
  5. washThe combined organic layers were washed with brine (30 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography (silica, 50% ethyl acetate to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a92ddd700fca4d6ba569b761a2cbc07a
Source dataset
uspto-grants-2016_02
Patent number
US09249123B2

Reaction notes

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