Triphenylphosphine → HCID 69434719, compound

HRID 404901Notes

Reaction equation

HRID 404901 reaction equation
[Cl:1][C:2]1[CH:31]=[C:30]([OH:32])[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[S:6][C:7]([C:10]2[CH:14]=[C:13]([CH:15]([N:17]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]3=[O:27])[CH3:16])[O:12][N:11]=2)=[CH:8][N:9]=1.[CH:33]1([CH2:36]O)[CH2:35][CH2:34]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:1][C:2]1[CH:31]=[C:30]([O:32][CH2:36][CH:33]2[CH2:35][CH2:34]2)[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[S:6][C:7]([C:10]2[CH:14]=[C:13]([CH:15]([N:17]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]3=[O:27])[CH3:16])[O:12][N:11]=2)=[CH:8][N:9]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75644CyclopropanemethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 69435771HCID 69435771, compound

Product 1

HCID 69434719HCID 69434719, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 30F (550 mg, 1.18 mmol), cyclopropylmethanol (0.14 mL, 1.76 mmol) and triphenylphosphine (462 mg, 1.76 mmol) in tetrahydrofuran (10 mL) was added diethyl azodicarboxylate (0.28 mL, 1.76 mmol) at ambient temperature. The reaction was stirred for 16 hours, concentrated and purified by flash chromatography on silica gel eluting with a solvent gradient from 10% to 30% ethyl acetate in hexanes to provide 480 mg of the title compound as a white solid (78%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.28-0.39 (m, 2H) 0.53-0.65 (m, 2H) 1.12-1.30 (m, 1H) 1.82 (d, J=7.35 Hz, 3H) 3.88 (d, J=6.99 Hz, 2H) 5.56-5.69 (m, J=7.11, 7.11, 7.11 Hz, 1H) 7.03 (dd, J=8.82, 2.94 Hz, 1H) 7.17 (s, 1H) 7.23 (d, J=2.94 Hz, 1H) 7.53 (d, J=8.82 Hz, 1H) 7.83-7.97 (m, 5H); MS (ESI) m/z 522.1 (M+H)+

Workup

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

Sources & evidence

ORD record
ord-c39128d5e89a4b8faece96b08e96c951
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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