2-(Dimethylamino)ethanol → Methyl[{[4-(2-butynyloxy)phenyl]-sulfonyl}(methyl)amino]{4-[2-(dimethylamino)ethoxy]phenyl}acetate

HRID 2084898Notes

Reaction equation

HRID 2084898 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][OH:24].[CH2:26]([O:30][C:31]1[CH:36]=[CH:35][C:34]([S:37]([N:40]([CH:42]([C:47]2[CH:52]=[CH:51][C:50](O)=[CH:49][CH:48]=2)[C:43]([O:45][CH3:46])=[O:44])[CH3:41])(=[O:39])=[O:38])=[CH:33][CH:32]=1)[C:27]#[C:28][CH3:29].N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:46][O:45][C:43](=[O:44])[CH:42]([N:40]([S:37]([C:34]1[CH:35]=[CH:36][C:31]([O:30][CH2:26][C:27]#[C:28][CH3:29])=[CH:32][CH:33]=1)(=[O:38])=[O:39])[CH3:41])[C:47]1[CH:52]=[CH:51][C:50]([O:24][CH2:23][CH2:22][N:21]([CH3:25])[CH3:20])=[CH:49][CH:48]=1

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86587121Methyl [{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino](4-hydroxyphenyl)acetate

Product 1

HCID 131722538Methyl[{[4-(2-butynyloxy)phenyl]-sulfonyl}(methyl)amino]{4-[2-(dimethylamino)ethoxy]phenyl}acetateYield 52.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.390 g (1.489 mmol) of triphenylphosphine in 8 mL of THF was added 0.150 mL (1.489 mmol) of N,N-dimethylethanolamine followed by 0.400 g (0.993 mmol) of methyl [{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino](4-hydroxyphenyl)acetate (from Example 179) and 0.234 mL (1.489 mmol) of diethyl azodicarboxylate. The reaction was stirred overnight at room temperature and then concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3) to give 0.246 g of methyl[{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino]{4-[2-(dimethylamino)ethoxy]phenyl}acetate as a white solid. Electrospray Mass Spec 475.2 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3)

Sources & evidence

ORD record
ord-c085566b619a4875ab0dd029865b7bee
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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