Triphenylphosphine → HCID 11530538, compound

HRID 1867277Notes

Reaction equation

HRID 1867277 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[N:15]12[CH2:23][CH2:22][CH:19]([CH2:20][CH2:21]1)[N:18]([C:24]([C:26]1[C:30]3[CH:31]=[CH:32][C:33]([OH:35])=[CH:34][C:29]=3[S:28][N:27]=1)=[O:25])[CH2:17][CH2:16]2.[CH:36]1([CH2:39]O)[CH2:38][CH2:37]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH:36]1([CH2:39][O:35][C:33]2[CH:32]=[CH:31][C:30]3[C:26]([C:24]([N:18]4[CH:19]5[CH2:20][CH2:21][N:15]([CH2:23][CH2:22]5)[CH2:16][CH2:17]4)=[O:25])=[N:27][S:28][C:29]=3[CH:34]=2)[CH2:38][CH2:37]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 75644CyclopropanemethanolHCID 136174668HCID 136174668, compound

Product 1

HCID 11530538HCID 11530538, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (0.396 mmol) was added dropwise to a solution of 3-(1,4-diazabicyclo[3.2.2]non-4-ylcarbonyl)-1,2-benzisothiazol-6-ol (0.359 mmol), cyclopropyl carbinol (0.432 mmol), and triphenylphosphine (0.541 mmol) in tetrahydrofuran (2.2 mL). The reaction mixture was maintained at rt for 16 h, and then the reaction mixture was concentrated. The residue was purified by chromatography using a gradient of 50/50 to 0/100 ethyl acetate/[(70/30/1) ethylacetate/methanol/ammonium hydroxide)]. The compound was further purified by preparative HPLC to provide the product in 39% yield. 1H NMR (CD3OD) δ 8.06 and 8.05 (two d, J=9.0 ea, 1H), 7.56 (d, J=1.8, 1H), 7.14 and 7.13 (two dd, J=8.7, 2.2 ea, 1H), 5.00 (m, 0.79H), 4.50 (m, 0.34H), 4.25 (t, J=5.6, 0.68H), 4.09 (t, J=5.6, 1.34H), 3.95 (d, J=6.9, 2H), 3.63 (t, J=5.7, 0.70H), 3.62-3.36 (m, 5H), 2.45-2.37 (m, 2H), 2.26-2.02 (two m, 2H), 1.37-1.27 (m, 1H), 0.69-0.62 (m, 2H), 0.42-0.37 (m, 2H); LC/MS (EI) tR3.91 min, m/z 358 (M++1).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe residue was purified by chromatography
  3. customThe compound was further purified by preparative HPLC
  4. customto provide the product in 39% yield

Sources & evidence

ORD record
ord-694c99eb9f2a425f8e81a3d6513b3b08
Source dataset
uspto-grants-2009_12
Patent number
US07632831B2

Reaction notes

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