Triphenylphosphine → HCID 24992097, compound

HRID 423558Notes

Reaction equation

HRID 423558 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:28][CH:29]([C:31]1[N:35]=[C:34]([N:36]2[CH2:41][CH2:40][CH:39]([CH2:42]O)[CH2:38][CH2:37]2)[O:33][N:32]=1)[CH3:30].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:30][CH:29]([C:31]1[N:35]=[C:34]([N:36]2[CH2:37][CH2:38][CH:39]([CH2:42][O:1][C:2]3[CH:7]=[CH:6][C:5]([C:8]4[CH:9]=[CH:10][C:11]([S:14]([NH:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])(=[O:15])=[O:16])=[CH:12][CH:13]=4)=[CH:4][CH:3]=3)[CH2:40][CH2:41]2)[O:33][N:32]=1)[CH3:28]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 57930076{1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methanolHCID 86638739HCID 86638739, compound

Product 1

HCID 24992097HCID 24992097, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound (169 mg, 45%) was prepared as a white solid from 1,1-dimethylethyl (2-{[(4′-hydroxy-4-biphenylyl)sulfonyl]amino}ethyl)carbamate (246 mg, 0.63 mmol), {1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methanol (prepared as in Example 20, Step 3, 214 mg, 0.95 mmol) and Ph3P (249 mg, 0.95 mmol) in THF (5 mL) followed by diisopropyl azodicarboxylate (0.187 mL, 0.95 mmol) in a manner similar to Example 1, Step 2. 1H NMR (400 MHz, DMSO-d6) δ 7.84-7.72 (m, 4H), 7.70-7.60 (m, 3H), 7.03 (d, 2H, J=8.8 Hz), 6.76 (t, 1H, J=5.4 Hz), 4.03-3.91 (m, 2H), 3.90 (d, 2H, J=6.4 Hz), 3.15-3.05 (m, 2H), 2.98-2.88 (m, 2H), 2.83-2.67 (m, 3H), 2.06-1.94 (m, 1H), 1.89-1.79 (m, 2H), 1.38-1.24 (m, 11H), 1.14 (d, 6H, J=7.0 Hz); LRMS (ESI), m/z 600 (M+H).

Sources & evidence

ORD record
ord-27f98098fc004f60912e416e509c2bc6
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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