2-(Dimethylamino)ethanol → HCID 86601379, compound

HRID 852926Notes

Reaction equation

HRID 852926 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:34])[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][NH:23][C:24]2[S:25][C:26]3[CH:32]=[C:31]([OH:33])[CH:30]=[CH:29][C:27]=3[N:28]=2)=[CH:18][CH:17]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:36][N:37]([CH3:41])[CH2:38][CH2:39]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:34])[C:16]1[CH:17]=[CH:18][C:19]([CH2:22][NH:23][C:24]2[S:25][C:26]3[CH:32]=[C:31]([O:33][CH2:39][CH2:38][N:37]([CH3:41])[CH3:36])[CH:30]=[CH:29][C:27]=3[N:28]=2)=[CH:20][CH:21]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 86601378HCID 86601378, compound

Product 1

HCID 86601379HCID 86601379, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of compound 129 (1.00 g, 2.04 mmol) in THF (6.8 mL) at room temperature under N2 atmosphere were successively added N,N-dimethylethanolamine (225 μl, 2.24 mmol) and triphenylphosphine (696 mg, 2.65 mmol) followed by diisopropyl azodicarboxylate (550 μL, 2.65 mmol). Heat was evolved and the mixture turned dark red. It was stirred for 4 h, THF was removed in vacuo and the dark residue was partitioned between EtOAc and H2O. Organic phase was collected and extracted with HCl 1N. Acidic extract was separated and neutralized with saturated aqueous NaHCO3 under vigorous stirring. A white precipitate was formed which was collected by filtration to afford the title compound 133 (430 mg, 37% yield). 1H NMR: (acetone-d6) δ (ppm): 7.99 (d, J=8.4 Hz, 2H), 7.70 (dd, J=8.0, 2.2 Hz, 1H), 7.59 (d, J=8.4 Hz, 2H), 7.56 (d, J=1.6 Hz, 1H), 7.33 (d, J=9.0 Hz, 1H), 7.27 (d, J=2.5 Hz, 1H), 7.19 (quint.d, J=7.8, 2.4 Hz, 2H), 6.87 (dd, J=8.8, 2.5 Hz, 1H), 4.80 (s, 2H), 4.08 (t, J=5.9 Hz, 2H), 2.67 (t, J=5.7 Hz, 2H), 2.27 (s, 6H), 1.48 (s, 9H). m/z: 562.5 (MH+).

Workup

  1. temperatureHeat
  2. customTHF was removed in vacuo
  3. customthe dark residue was partitioned between EtOAc and H2O
  4. customOrganic phase was collected
  5. extractionextracted with HCl 1N
  6. extractionAcidic extract
  7. customwas separated
  8. customA white precipitate was formed which
  9. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-17229771bc7644078b221e9f078c998d
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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