Triphenylphosphine → 2-[4-(4-Fluoro-benzyloxy)-benzenesulfonylamino]-oxo-heptanoic acid tert-butyl ester

HRID 2269321Notes

Reaction equation

HRID 2269321 reaction equation
[C:1]([CH:4](O)[CH2:5][CH3:6])(=[O:3])C.[C:8]([O:12][C:13](=[O:34])[CH2:14][NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:21][CH:20]=1)(=[O:18])=[O:17])([CH3:11])([CH3:10])[CH3:9].[C:35]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:8]([O:12][C:13](=[O:34])[CH:14]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C:1](=[O:3])[CH2:4][CH2:5][CH2:6][CH3:35])([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 624843-Hydroxy-2-pentanone2×HCID 5462977Diethyl azodicarboxylate2×HCID 54478351[4-(4-Fluoro-benzyloxy)-benzenesulfonylamino]-acetic acid tert-butyl ester

Product 1

HCID 702138282-[4-(4-Fluoro-benzyloxy)-benzenesulfonylamino]-oxo-heptanoic acid tert-butyl esterYield 57.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of acetyl propanol (0.39 mL, 3.8 mmol), [4-(4-fluoro-benzyloxy)-benzenesulfonylamino]-acetic acid tert-butyl ester (1.0 g, 2.53 mmol) and tetrahydrofuran (8 mL) was added triphenylphosphine (1.0 g, 3.8 mmol) and diethylazodicarboxylate (0.60 mL, 3.8 mmol). After stirring for 6 h at room temperature, the mixture was treated with additional acetyl propanol (0.15 mL), triphenyl phosphine (0.30 g) and diethylazodicarboxylate (0.20 mL). After stirring for 30 min, the mixture was concentrated in vacuo, and the residue was purified by silica gel chromatography eluting with 4:1 to 2:1 hexane-ethyl acetate, giving 0.70 g of 2-[4-(4-fluoro-benzyloxy)-benzenesulfonylamino]-oxo-heptanoic acid tert-butyl ester as a colorless solid:

Workup

  1. stirringAfter stirring for 30 min
  2. concentrationthe mixture was concentrated in vacuo
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with 4:1 to 2:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-e60ef466ecab44a6be4714fc293b9687
Source dataset
uspto-grants-2001_12
Patent number
US06329397B1

Reaction notes

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