Potassium Carbonate → HCID 86718412, compound

HRID 1755206Notes

Reaction equation

HRID 1755206 reaction equation
C([O:4][C@@H:5]([CH3:38])/[CH:6]=[CH:7]\[C:8]([NH:10][C@H:11]1[C@@H:16]([CH3:17])[O:15][C@@H:14]([CH2:18]/[CH:19]=[C:20](\[CH3:36])/[CH:21]=[CH:22]/[C@@H:23]2[CH2:30][C@@:27]3([O:29][CH2:28]3)[CH2:26][C@@H:25]([CH2:31][C:32]([O:34][CH3:35])=[O:33])[O:24]2)[C@@H:13]([CH3:37])[CH2:12]1)=[O:9])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:4][C@@H:5]([CH3:38])/[CH:6]=[CH:7]\[C:8]([NH:10][C@H:11]1[C@@H:16]([CH3:17])[O:15][C@@H:14]([CH2:18]/[CH:19]=[C:20](\[CH3:36])/[CH:21]=[CH:22]/[C@@H:23]2[CH2:30][C@@:27]3([O:29][CH2:28]3)[CH2:26][C@@H:25]([CH2:31][C:32]([O:34][CH3:35])=[O:33])[O:24]2)[C@@H:13]([CH3:37])[CH2:12]1)=[O:9]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86718413HCID 86718413, compound

Product 1

HCID 86718412HCID 86718412, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Synthesis of methyl [(3S,5S,7S)-7-{(1E,3E)-5-[(2S,3S,5R,6R)-5-{[(2Z,4S)-4-hydroxypent-2-enoyl]amino}-3,6-dimethyltetrahydro-2H-pyran-2-yl]-3-methylpenta-1,3-dien-1-yl}-1,6-dioxaspiro[2.5]oct-5-yl]acetate (#B148). To a solution of the crude material from Step 1 of example A#50 in methanol (3.5 mL) at rt was added potassium carbonate (136 mg, 0.056 mmol, 2.5 eq.), and the reaction was stirred for 2 hours. The reaction was filtered with methanol, diluted with dimethyl sulfoxide (2 mL), and concentrated in vacuo. Purification by reverse phase medium pressure liquid chromatography eluted with 0.02% acetic acid in water (v/v) and 0.02% acetic acid in acetonitrile (v/v) (10% to 90%) provided #B148 as a white solid. Yield: 91.6 mg, 0.18 mmol, 48%. LCMS (Protocol D): m/z 492.47 [M+H]+, retention time=0.80 minutes. 1H NMR (400 MHz, DMSO-d6) δ 7.76 (d, J=7.8 Hz, 1H), 6.25 (d, J=16.0 Hz, 1H), 5.97 (d, J=11.9 Hz, 1H), 5.87 (d, J=11.9 and 7.0 Hz, 1H), 5.65-5.48 (m, 2H), 5.22-5.13 (m, 1H), 5.10 (d, J=4.7 Hz, 1H), 4.56-4.48 (m, 1H), 4.36-4.25 (m, 1H), 3.69-3.61 (m, 2H), 3.60 (s, 3H), 3.55-3.46 (m, 1H), 2.74-2.56 (m, 4H), 2.38-2.13 (m, 2H), 1.90-1.60 (m, 9H), 1.44 (dd, J=13.2 and 7.0 Hz, 1H), 1.11 (d, J=6.2 Hz, 3H), 1.06 (d, J=6.2 Hz, 3H), 0.96 (d, J=7.0 Hz, 3H).

Workup

  1. customat rt
  2. filtrationThe reaction was filtered with methanol
  3. additiondiluted with dimethyl sulfoxide (2 mL)
  4. concentrationconcentrated in vacuo
  5. customPurification by reverse phase medium pressure liquid chromatography
  6. washeluted with 0.02% acetic acid in water (v/v) and 0.02% acetic acid in acetonitrile (v/v) (10% to 90%)
  7. customprovided #B148 as a white solid

Sources & evidence

ORD record
ord-ca70c28ba8f646b6a7076004fff0bf64
Source dataset
uspto-grants-2015_10
Patent number
US09169264B2

Reaction notes

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