Water → HCID 71547804, compound

HRID 1184554Notes

Reaction equation

HRID 1184554 reaction equation
[CH2:1]1[NH:6][CH2:5][CH2:4][N:3]2[CH2:7][C@@H:8]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)(=[O:13])=[O:12])[CH2:9][C@@H:2]12.C(=O)([O-])[O-].[Na+].[Na+].I[CH:31]([CH3:33])[CH3:32].O>CS(C)=O>[CH:31]([N:6]1[CH2:5][CH2:4][N:3]2[CH2:7][C@@H:8]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[CH:15]=3)(=[O:13])=[O:12])[CH2:9][C@H:2]2[CH2:1]1)([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 10340Sodium CarbonateHCID 71547802HCID 71547802, compound

Product 1

HCID 71547804HCID 71547804, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of Example 42 (30 mg, 0.078 mmol) in dimethyl sulfoxide (1 mL) was added sodium carbonate (8.24 mg, 0.078 mmol) and 2-iodopropane (13.22 mg, 0.078 mmol). The mixture was stirred at room temperature for 3 days. The mixture was poured into 10 mL water, and the crude product was extracted with dichloromethane (3×8 mL). The combined organic fractions were concentrated. The residue was purified by chromatography on silica gel (dichloromethane/methanol=10:1) to give the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 0.91 (dd, 6H, J=7 Hz), 1.10 (m, 1H), 1.85 (m, 3H), 2.12 (m, 1H), 2.22 (m, 1H), 2.69 (m, 3H), 3.69 (m, 4H), 7.85 (m, 1H), 8.06 (m, 3H); MS (ESI) m/z 392 (M+H)+.

Workup

  1. extractionthe crude product was extracted with dichloromethane (3×8 mL)
  2. concentrationThe combined organic fractions were concentrated
  3. customThe residue was purified by chromatography on silica gel (dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-0b82a831b5204133814a2b7d4679b98b
Source dataset
uspto-grants-2014_03
Patent number
US08669255B2

Reaction notes

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