HCID 70913855, compound → HCID 70913850, compound

HRID 1844746Notes

Reaction equation

HRID 1844746 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:16]2[N:20]([CH2:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[C:19]([CH3:28])=[C:18]([S:29]([NH2:32])(=[O:31])=[O:30])[CH:17]=2)[CH:7]=[C:8]2[C:13]3([CH2:15][CH2:14]3)[CH2:12][CH2:11][O:10][C:9]=12)(=[O:3])[CH3:2].[CH3:33][Mg+].[Br-]>C1COCC1>[CH:22]1([CH2:21][N:20]2[C:16]([C:6]3[CH:7]=[C:8]4[C:13]5([CH2:15][CH2:14]5)[CH2:12][CH2:11][O:10][C:9]4=[C:4]([C:1]([OH:3])([CH3:33])[CH3:2])[CH:5]=3)=[CH:17][C:18]([S:29]([NH2:32])(=[O:30])=[O:31])=[C:19]2[CH3:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 70913855HCID 70913855, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 70913850HCID 70913850, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of compound 36 (86 mg, 0.19 mmol) in dry THF (2 mL) was added CH3MgBr (3M, 70 μL, 0.21 mmol) and the mixture was stirred at rt for 2 h, quenched with aq. NH4Cl at 0° C. and extracted with EA. The organic layer was concentrated and purified by CC (PE/EE=4/1) to give compound 37 (21 mg, 24%) as a colorless solid. 1H-NMR (CDCl3+D2O, 400 MHz) δ: 0.67-0.72 (2H, m), 0.88-0.91 (2H, m), 1.01-1.05 (5H, m), 1.36-1.44 (3H, m), 1.60 (9H, m), 1.93-1.95 (2H, t, J=10.4 Hz), 2.52 (3H, s), 3.63-3.65 (2H, d, J=7.2 Hz), 4.43-4.45 (2H, t, J=10.4 Hz), 6.35 (1H, s), 6.49 (1H, s), 6.98 (1H, s). MS Calcd.: 472; MS Found: 473 (M+1)+.

Workup

  1. customquenched with aq. NH4Cl at 0° C.
  2. extractionextracted with EA
  3. concentrationThe organic layer was concentrated
  4. custompurified by CC (PE/EE=4/1)

Sources & evidence

ORD record
ord-f50c6ca3e1304a9f882e1ab544b7936b
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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