Indoline → HCID 68085203, compound

HRID 78740Notes

Reaction equation

HRID 78740 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]([CH2:15][CH:16]([CH3:18])[CH3:17])/[CH:10]=[CH:11]/[C:12]([OH:14])=O)=[O:7])([CH3:4])[CH3:3].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH:55]1[C:63]2[C:58](=[CH:59][CH:60]=[CH:61][CH:62]=2)[CH2:57][CH2:56]1>CN(C=O)C.O>[N:55]1([C:12](=[O:14])/[CH:11]=[CH:10]/[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:15][CH:16]([CH3:18])[CH3:17])[C:63]2[C:58](=[CH:59][CH:60]=[CH:61][CH:62]=2)[CH2:57][CH2:56]1

Participants

7

Reactant 4

HCID 10328IndolineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 14081310(2E,4S)-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-6-methyl-2-heptenoic acid

Product 1

HCID 68085203HCID 68085203, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2E,4S)-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-6-methyl-2-heptenoic acid (4.70 g, 18.26 mmol) in DMF (30.0 mL) were added BOP reagent (8.08 g, 18.26 mmol) and DIPEA (6.38 mL, 36.5 mmol). After stirring at RT for 5 min, 2,3-dihydro-1H-indole (2.053 mL, 18.26 mmol) was added and stirring continued overnight. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered, concentrated in vacuo and purified by flash column chromatography (0-20% EtOAc/hexanes) to afford the title compound (4.83 g, 74%) as a white solid. LC-MS m/z 359 (M+H)+, 1.18 min (ret time).

Workup

  1. stirringstirring continued overnight
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by flash column chromatography (0-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-71ac24e29c5140ca87d5b9dcfd21dc6b
Source dataset
uspto-grants-2014_09
Patent number
US08841463B2

Reaction notes

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