Water → HCID 23501774, compound

HRID 2228536Notes

Reaction equation

HRID 2228536 reaction equation
C([C:3]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[C:27](OCC2C=CC=CC=2)=[CH:26][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:19]([CH2:20][CH2:21][CH3:22])=[C:18]2[C:13]([CH2:14][CH2:15][CH:16](C(O)=O)[O:17]2)=[CH:12][CH:11]=1)C.[C:45]([OH:48])(=[O:47])[CH3:46].[C:49]([O:53][C:54]([NH:56][CH2:57][CH2:58]C(CN)C(O)=O)=[O:55])([CH3:52])([CH3:51])[CH3:50].O[C:66]1[C:74]2N=NN[C:70]=2[CH:69]=[CH:68][CH:67]=1.CN([C:78]([O:82]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([N:102]([CH:105](C)C)[CH2:103]C)(C)C.C1C=CC2N(O)N=N[C:112]=2[CH:113]=1.[OH2:118]>CN(C=O)C>[C:49]([O:53][C:54]([NH:56][CH2:57][CH2:58][O:47][C:45](=[O:48])[CH2:46][CH2:105][NH:102][C:103]([CH:16]1[CH2:15][CH2:14][C:13]2[C:18](=[C:19]([CH2:20][CH2:21][CH3:22])[C:10]([O:9][CH2:8][CH2:7][CH2:6][O:5][C:4]3[CH:26]=[C:27]([O:82][CH2:78][C:66]4[CH:74]=[CH:70][CH:69]=[CH:68][CH:67]=4)[C:28]([C:30]4[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=4)=[CH:29][C:3]=3[CH2:112][CH3:113])=[CH:11][CH:12]=2)[O:17]1)=[O:118])=[O:55])([CH3:50])([CH3:51])[CH3:52]

Participants

9

Reactant 7

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2×HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 23501765HCID 23501765, compoundHCID 86587144HCID 86587144, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 23501774HCID 23501774, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-(3-(2-ethyl-4-(4-flurophenyl)-5-(phenylmethoxy)phenoxy)propoxy)-8-propylchromane-2-carboxylic acid (200 mg, 0.33 mmol), 2-[N-t-butoxycarbonylaminoethyl]-3-aminopropionate acetate salt (122 mg, 0.42 mmol), hydroxybenzotriazole (76.6 mg, 0.50 mmol), HBTU (190 mg, 0.50 mmol), and diisopropylethylamine (1.32 mmol, 233 μL) were added to dry DMF (1.7 mL) and stirred under nitrogen for 24 hours. An additional 50% of HOBT, HBTU, and diisopropylethylamine were added and the reaction stirred another 24 hours. The mixture was added to water (7 mL) and extracted with ethyl acetate. The combined organics were washed with 0.1N HCl, bicarbonate, and brine, dried over MgSO4, filtered, and concentrated under vacuum. The resulting oil was purified by flash chromatography (hexane/ethyl acetate) to afford 120 mg of product. Mass Spec (EI) m/z=830.6 (M+NH4).

Workup

  1. stirringthe reaction stirred another 24 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined organics were washed with 0.1N HCl, bicarbonate, and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe resulting oil was purified by flash chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f2c6887132e045f2a43ab5092bc7f340
Source dataset
uspto-grants-2002_07
Patent number
US06416733B1

Reaction notes

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