Diketene → HCID 57609712, compound

HRID 416670Notes

Reaction equation

HRID 416670 reaction equation
[CH2:1]([O:8][C:9](=[O:21])[CH2:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OC1C=CC=CN=1.[CH2:29]=[C:30]1[O:34][C:32](=[O:33])[CH2:31]1>C1COCC1>[CH2:1]([O:8][C:9](=[O:21])[CH2:10][N:11]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1)[C:32](=[O:33])[CH2:31][C:30](=[O:34])[CH3:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 12661DiketeneHCID 426034HCID 426034, compoundHCID 178516071HCID 178516071, compound

Product 1

HCID 57609712HCID 57609712, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared according to the representative procedure (Method B) using (4-methoxy-benzylamino)-acetic acid benzyl ester (910 mg, 3.19 mmol), 2-hydroxypyridine (304 mg, 3.20 mmol) in THF (25 mL), and ketene dimer (1.0 mL, 16 mmol). Purification by flash chromatography on SiO2 (1:4 EtOAc/hexanes) gave keto ester 54e (930 mg, 78%) as a colorless oil. Due to the presence of enol tautomers and amide rotamers, the NMR spectra of this compound is extremely complex and so line listing is not provided. Rf=0.28 (33% EtOAc/hexanes); IR (neat) 1747, 1720, 1646 cm−1; LRMS (ESI) Calcd. for C21H23NO5 [M+H] 370, found 370; HRMS (ESI) Calcd. for C21H23NO5 [M+H] 370.1654, found 370.1655.

Workup

  1. customPrepared
  2. customPurification by flash chromatography on SiO2 (1:4 EtOAc/hexanes)

Sources & evidence

ORD record
ord-74f427685d3d4a9c90bac56f07a0373e
Source dataset
uspto-grants-2012_01
Patent number
US08088923B2

Reaction notes

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