Diisopropylethylamine → HCID 72556532, compound

HRID 2217628Notes

Reaction equation

HRID 2217628 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH:28]4[S:32][C:31](=[O:33])[NH:30][C:29]4=[O:34])=[CH:23][CH:22]=3)=[CH:16][CH:15]=2)[C:11]([OH:13])=[O:12])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C(N(CC)C(C)C)(C)C.CN([P+](O[N:55]1[N:63]=[N:62][C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][C:56]1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>ClCCl.C(OCC)(=O)C>[N:62]1([O:12][C:11](=[O:13])[C:10]([C:14]2[CH:15]=[CH:16][C:17]([O:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH:28]4[S:32][C:31](=[O:33])[NH:30][C:29]4=[O:34])=[CH:23][CH:22]=3)=[CH:18][CH:19]=2)=[CH:9][C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=2)[C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][C:56]=2[N:55]=[N:63]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 85330076HCID 85330076, compound

Product 1

HCID 72556532HCID 72556532, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 47 (0.81 g, 1.7 mmol) and N,N-diisopropylethylamine (0.33 mL, 1.9 mmol) in dichloromethane (20 mL) was added BOP reagent (0.76 g, 1.7 mmol). After 45 min of stirring at room temperature, the mixture was diluted with ethyl acetate (150 mL) then washed with 1N HCl (100 mL), water (100 mL), brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using hexanes:ethyl acetate (3:2). The solid obtained after concentration was further triturated with hexanes:ethyl acetate (4:1) to yield 0.75 g (76%) of 48.

Workup

  1. washthen washed with 1N HCl (100 mL), water (100 mL), brine (100 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography
  6. customThe solid obtained
  7. concentrationafter concentration
  8. customwas further triturated with hexanes:ethyl acetate (4:1)

Sources & evidence

ORD record
ord-8e4c1927bb354744a32983c3cc0f7410
Source dataset
uspto-grants-2008_08
Patent number
US07407978B2

Reaction notes

Loading…