HCID 86618000, compound → HCID 57987469, compound

HRID 1869761Notes

Reaction equation

HRID 1869761 reaction equation
C[CH:2]([C@H:6]1[CH2:11][CH2:10][N:9]([C@H:12]([C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][CH:19]=2)[CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C@@H:8]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)[CH2:7]1)[C:3]([O-:5])=[O:4]>CO>[I:24][C:21]1[CH:20]=[CH:19][C:18]([C@H:12]([N:9]2[CH2:10][CH2:11][C@@H:6]([CH2:2][C:3]([OH:5])=[O:4])[CH2:7][C@H:8]2[C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:27][CH:26]=2)[CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:23][CH:22]=1

Participants

3

Reactant 1

HCID 86618000HCID 86618000, compound

Product 1

HCID 57987469HCID 57987469, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ester from Step 1 (50 mg, 0.085 mmol) was stirred in MeOH (1 ml) at RT for 3 d. The reaction mixture was concentrated under reduced pressure and the residue partitioned between DCM and 2M HCl. The DCM layer was concentrated under reduced pressure to give the crude product, which was purified by flash chromatography (silica, 3% MeOH in DCM) to give the title compound, 28 mg (57%). 1H NMR (500 MHz, CDCl3) δ (ppm) 0.58-0.66 (1H, m), 0.81-0.83 (6H, m), 0.86-0.95 (1H, m), 1.14 (1H, dq, J 3.8, 12.1), 1.34 (1H, q, J 12.1), 1.42 (1H, septet, J 6.5), 1.74-1.76 (3H, m), 1.84 (1H, br, d, J 12.7), 2.16-2.29 (2H, m), 2.33 (1H, dt, J 2.2, 12.1), 2.69 (1H, td, J 3.6, 12.1), 3.35 (1H, dd, J 5.1, 9.9), 3.72 (1H, dd, J 2.5, 10.9), 6.98 (2H, d, J 8.1), 7.54 (2H, br, d, J 7.45), 7.59-7.63 (4H, m); M/Z (ES+) 574 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue partitioned between DCM and 2M HCl
  3. concentrationThe DCM layer was concentrated under reduced pressure
  4. customto give the crude product, which
  5. customwas purified by flash chromatography (silica, 3% MeOH in DCM)

Sources & evidence

ORD record
ord-0ba0bf87b378478b9930bee6454e1918
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

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