HCID 68157546, compound → HCID 68157745, compound

HRID 242827Notes

Reaction equation

HRID 242827 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]([C:10](=O)[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][CH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O>[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]([C:10]1[N:18]([CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 68157546HCID 68157546, compound

Product 1

HCID 68157745HCID 68157745, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

{(S)-1-[2-(Tetrahydropyran-4-ylamino)phenylcarbamoyl]ethyl}carbamic acid tertbutyl ester (1.90 g, 5.23 mmol) was dissolved in AcOH (30 mL) and heated to 70° C. for 18 h. Volatiles were then removed in vacuo and the residue was partitioned between DCM and a saturated solution of NaHCO3. The aqueous phase was further extracted with DCM (×2) and the combined organic layers were then washed with brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-4% 2M NH3/MeOH in DCM) affording {(S)-1-[1-(Tetrahydropyran-4-yl)-1H-benzoimidazol-2-yl]ethyl}carbamic acid tertbutyl ester as a white foam (1.40 g, 77%). LCMS: RT 2.23 min [M+H-tBu]+ 290.1.

Workup

  1. customVolatiles were then removed in vacuo
  2. customthe residue was partitioned between DCM
  3. extractionThe aqueous phase was further extracted with DCM (×2)
  4. washthe combined organic layers were then washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-4% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-06ec5aa15f334f3986986929251be40f
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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