Triphenylphosphine → N-methoxy-N-methyl-3-{2-[2-(2-triisopropylsilanyloxy-naphthalen-1-yl)-ethoxy]-benzenesulfonylamino}-succinamic acid tert-butyl ester

HRID 1814337Notes

Reaction equation

HRID 1814337 reaction equation
[CH:1]([Si:4]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[CH2:16][CH2:17][OH:18])([CH3:3])[CH3:2].[C:25]([O:29][C:30](=[O:50])[CH2:31][C@H:32]([NH:39][S:40]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1O)(=[O:42])=[O:41])[C:33]([N:35]([O:37][CH3:38])[CH3:36])=[O:34])([CH3:28])([CH3:27])[CH3:26].CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:25]([O:29][C:30](=[O:50])[CH2:31][CH:32]([NH:39][S:40]([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][C:48]=1[O:18][CH2:17][CH2:16][C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]=[CH:15][C:6]=1[O:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:19]([CH3:21])[CH3:20])[CH:22]([CH3:24])[CH3:23])(=[O:42])=[O:41])[C:33]([N:35]([O:37][CH3:38])[CH3:36])=[O:34])([CH3:28])([CH3:26])[CH3:27]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 225040152-(2-Triisopropylsilanyloxy-naphthalen-1-yl)-ethanolHCID 86588199(S)-3-(2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester

Product 1

HCID 86588230N-methoxy-N-methyl-3-{2-[2-(2-triisopropylsilanyloxy-naphthalen-1-yl)-ethoxy]-benzenesulfonylamino}-succinamic acid tert-butyl esterYield 69.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Triisopropylsilanyloxy-naphthalen-1-yl)-ethanol (1.0 g, 2.91 mmol) was mixed with (S)-3-(2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester (1.13 g, 2.91 mmol), diethylazodicarboxylate (0.92 mL, 5.8 mmol), and triphenyl phosphine (1.52 g, 5.82 mmol) in THF (18.6 mL) at room temperature for 16 h. The reaction mixture was concentrated onto SiO2 (˜3 g) and then was chromatographed over SiO2 with 20% EtOAc/hexane to give N-methoxy-N-methyl-3-{2-[2-(2-triisopropylsilanyloxy-naphthalen-1-yl)-ethoxy]-benzenesulfonylamino}-succinamic acid tert-butyl ester (1.45 g, 2.03 mmol) as an oil in 69% yield. MS (APCI) m/z 715.4 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated onto SiO2 (˜3 g)
  2. customwas chromatographed over SiO2 with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-1e8d87ce75ed402a844fdeabf55decac
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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