Benzyl Alcohol → HCID 69464031, compound

HRID 350615Notes

Reaction equation

HRID 350615 reaction equation
[C:1]([O:5][C:6](=[O:29])[CH2:7][CH:8]([NH:11][C:12]([O:14][CH2:15][CH:16]1[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[CH:9]=[O:10])([CH3:4])([CH3:3])[CH3:2].[CH3:30][C:31]1[CH:32]=[CH:33][C:34](S(O)(=O)=O)=[CH:35][CH:36]=1.O.[CH2:42]([OH:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>ClCCl>[C:1]([O:5][C:6](=[O:29])[CH2:7][CH:8]([NH:11][C:12]([O:14][CH2:15][CH:16]1[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[CH:9]([O:49][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[O:10][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 521998p-Toluenesulfonic acid monohydrateHCID 22744159HCID 22744159, compound

Product 1

HCID 69464031HCID 69464031, compoundYield 200.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-oxo-butyric acid tert-butyl ester (1.24 g, 3.14 mmol) in Dichloromethane (10 mL) at room temperature was added 0.20 equiv TsOH.H2O (0.12 g, 0.63 mmol) and followed by dropwise 5.0 equiv of Benzyl alcohol (1.62 mL, 15.68 mmol). After stirring room temperature for 18 hrs, the reaction mixture was filtered through celite and the filtrate was concentrated in vacuo to obtain a crude title compound. The residue was purified by flask column chromatography on silica gel eluting with EtOAc/Hexane (10–40%) to give the title compound (0.75 g, 40%) as clear oil. TLC (40% EtOAc/Hexane) Rf=0.68; 1HNMR (CDCl3) δ 7.76 (d, J=7.2 Hz, 2H), 7.59 (d, J=7.5 Hz, 2H), 7.39 (t, J=7.5 Hz, 21H), 7.35–7.27 (m, 12H), 5.37 (d, J=9.6 Hz, 1H), 4.73–4.52 (m, 5H), 4.35 (d, J=6.6 Hz, 2H), 4.24–4.16 (q, J=6.6 Hz, 2H), 2.55–2.50 (m, 2H), 1.39 (s, 9H). MS(ES) for C37H39NO9 (MW=593.71): positive 611 (M+NH4+).

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto obtain a crude title compound
  4. customThe residue was purified by flask column chromatography on silica gel eluting with EtOAc/Hexane (10–40%)

Sources & evidence

ORD record
ord-ab5b4e29c2ad40e789d9b28ac1580fa4
Source dataset
uspto-grants-2007_02
Patent number
US07183260B2

Reaction notes

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