Diethyl Ether → HCID 86741333, compound

HRID 1905774Notes

Reaction equation

HRID 1905774 reaction equation
C[N:2]([C:10]1([CH2:15][CH3:16])[O:14][CH2:13][CH2:12][O:11]1)[C@H:3]([C:7]([OH:9])=[O:8])[CH:4]([CH3:6])[CH3:5].[CH2:17](N(CC)CC)C.[F:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1.CCOCC>ClCCl>[CH3:17][C@@:3]([C:7]([OH:9])=[O:8])([CH:4]([CH3:5])[CH3:6])[N:2]([C:29](=[O:30])[C:28]1[CH:32]=[CH:33][C:25]([F:24])=[CH:26][CH:27]=1)[C:10]1([CH2:15][CH3:16])[O:11][CH2:12][CH2:13][O:14]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 70447083HCID 70447083, compound

Product 1

HCID 86741333HCID 86741333, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of Methyl-N-[2-(2-ethyl)-1,3-dioxolanyl]valine (3 g, 13 mmoles) and triethylamine (3.6 ml, 26 mmoles) in 20 ml of dichloromethane (CH2CL2) cooled to 0° C. was added a solution of 4-fluorobenzoyl chloride (1.65 ml, 14 mmoles) in 10 ml of (CH2CL2). The solution was stirred 60 minutes at 0° C. and 60 minutes at room temperature. It was then poured into ether and washed with water, saturated aq. bicarbonate, brine, and dried (MgSO4). Flash chromatography on silica gel eluting with 1:1 hexane-ethyl acetate provided 3 g of the title compound. 90 MHz NMR (CDCl3) δ 0.90, (brd, J=7 Hz, 6H), 1.8-2.5 (m, 3H), 3.45 (br, dd, J=6, 8 Hz, 1H), 3.72 (s, 3H), 3.80 (m, 6H), 4.80 (m, 1H), 6.9-7.5 (m, 4H).

Workup

  1. washwashed with water, saturated aq. bicarbonate, brine
  2. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-284937c6c9e440818ebdb08b3487b98d
Source dataset
uspto-grants-1987_03
Patent number
US04647576

Reaction notes

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