Diisopropylethylamine → HCID 131733881, compound

HRID 708924Notes

Reaction equation

HRID 708924 reaction equation
[ClH:1].Cl.[F:3][C:4]1[CH:5]=[C:6]([CH:8]=[C:9]([CH2:17][NH:18][CH3:19])[C:10]=1[O:11][C@@H:12]1[CH2:16][CH2:15][O:14][CH2:13]1)[NH2:7].CCN(C(C)C)C(C)C.[CH2:29]([O:36][C:37]([O:39]N1C(=O)CCC1=O)=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C=O)C>[ClH:1].[NH2:7][C:6]1[CH:5]=[C:4]([F:3])[C:10]([O:11][C@@H:12]2[CH2:16][CH2:15][O:14][CH2:13]2)=[C:9]([CH:8]=1)[CH2:17][N:18]([CH3:19])[C:37](=[O:39])[O:36][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 83172Benzyl succinimido carbonateHCID 131733882HCID 131733882, compound

Product 1

HCID 131733881HCID 131733881, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 38B (200 mg, 0.639 mmol) and DIEA (0.445 ml, 2.55 mmol) in DMF (10 mL), was added N-(benzyloxycarbonyloxy) succinimide (167 mg, 0.671 mmol). The mixture was stirred at rt for 1 h, then quenched with H2O. The mixture was extracted with EtOAc (3×) and the organic layer was washed with 1N HCl, sat. NaHCO3, brine, and dried over Na2SO4. The crude was purified by flash column chromatography (0-60% EtOAc/hexanes) to give 38C (182 mg, 0.486 mmol, 76% yield). MS (ESI) m/z: 375.3 (M+H)+.

Workup

  1. customquenched with H2O
  2. extractionThe mixture was extracted with EtOAc (3×)
  3. washthe organic layer was washed with 1N HCl, sat. NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. customThe crude was purified by flash column chromatography (0-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-00fe46b6d9844773a150766909e1bd79
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

Loading…