HCID 86727207, compound → HCID 86727208, compound

HRID 2274317Notes

Reaction equation

HRID 2274317 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@H:14]2[NH:15][C:16](=[O:18])[O:17][C@H:13]2[CH2:12][C@H:11]([CH:19]=[O:20])[C@H:10]1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][Mg]Cl>C1COCC1>[CH2:1]([O:8][C@@H:9]1[C@H:14]2[NH:15][C:16](=[O:18])[O:17][C@H:13]2[CH2:12][C@H:11]([CH:19]([OH:20])[CH3:29])[C@H:10]1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 86727207HCID 86727207, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 86727208HCID 86727208, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the above crude 3 (1.4 g, 3.6 mmol) in THF (10 mL) was added methylmagnesium chloride (7.0 mL, 2.5M in THF, 17.5 mmol) at −78° C. After 1 hour, the reaction mixture was quenched with saturated aqueous NH4Cl (20 mL) and extracted with DCM (4×50 mL). The combined organic layer was dried over anhydrous MgSO4 and concentrated in vacuo to give a residue, which was purified by a silica gel column, eluted with 10% MeOH in DCM to give 4 as a white solid (1.0 g, 68% in two steps, the ratio of diastereomers is 1:3 by 1H NMR). (ES, m/z): [M+H]+ 397.9; 1H NMR (300 MHz, CDCl3) δ 7.30-7.45 (m, 10H), 4.91-4.96 (m, 2H), 4.70-4.87 (m, 2H), 4.50-4.69 (m, 2H), 3.74-3.79 (m, 2H), 3.47-3.58 (m, 2H), 1.50-1.76 (m, 2H), 1.15 (d, J=6.6 Hz, 3H).

Workup

  1. customthe reaction mixture was quenched with saturated aqueous NH4Cl (20 mL)
  2. extractionextracted with DCM (4×50 mL)
  3. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customto give a residue, which
  6. customwas purified by a silica gel column
  7. washeluted with 10% MeOH in DCM

Sources & evidence

ORD record
ord-487ffa60057d4612ad687db647fdd42d
Source dataset
uspto-grants-2015_09
Patent number
US09126957B2

Reaction notes

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