Isopropanol → HCID 69438229, compound

HRID 404926Notes

Reaction equation

HRID 404926 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[O:5][C:6]1[S:7][C:8]([C:11]2[CH:15]=[C:14]([CH:16]([N:18]3[C:26](=[O:27])[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]3=[O:28])[CH3:17])[O:13][N:12]=2)=[CH:9][N:10]=1.[CH:32](O)([CH3:34])[CH3:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH:32]([O:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[O:5][C:6]1[S:7][C:8]([C:11]2[CH:15]=[C:14]([CH:16]([N:18]3[C:26](=[O:27])[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]3=[O:28])[CH3:17])[O:13][N:12]=2)=[CH:9][N:10]=1)([CH3:34])[CH3:33]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 69436441HCID 69436441, compound

Product 1

HCID 69438229HCID 69438229, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 86F (250 mg, 0.68 mmol), isopropanol (78 μL, 1.02 mmol) and triphenylphosphine (267 mg, 1.02 mmol) in tetrahydrofuran (5 mL) was added diethyl azodicarboxylate (175 μL, 1.02 mmol) at 25° C. The reaction was stirred for 16 hours and concentrated. The concentrate was purified by flash chromatography on silica gel eluting with a solvent gradient from 10% to 30% ethyl acetate in hexanes to provide 272 mg of the title compound (84%) as a off-white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.26 (d, J=5.88 Hz, 6H) 1.82 (d, J=6.99 Hz, 3H) 4.55-4.74 (m, 1H) 5.64 (q, J=6.99 Hz, 1H) 6.83-7.05 (m, 3H) 7.18 (s, 1H) 7.38 (t, J=8.27 Hz, 1H) 7.83-7.95 (m, 4H) 7.96 (s, 1H); MS (ESI) m/z 476.1 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by flash chromatography on silica gel eluting with a solvent gradient from 10% to 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-32adb98eb16f47bb9d29d0e07541811c
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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