Vinyl chloroformate → HCID 15928270, compound

HRID 1073093Notes

Reaction equation

HRID 1073093 reaction equation
[C:1]([CH2:3][C@H:4]1[CH2:9][CH2:8][N:7](CC=C)[C@@H:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:5]1)#[N:2].Cl[C:19]([O:21][CH:22]=[CH2:23])=[O:20].CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1>ClCCl>[C:1]([CH2:3][C@H:4]1[CH2:9][CH2:8][N:7]([C:19]([O:21][CH:22]=[CH2:23])=[O:20])[C@@H:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:5]1)#[N:2]

Participants

5

Reactant 3

HCID 78808Vinyl chloroformateHCID 88675Proton spongeHCID 15666796HCID 15666796, compound

Product 1

HCID 15928270HCID 15928270, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.0 g of the product from step C above, 1.8 g (16.5 mmol) of vinyl chloroformate and 3.5 g (16.5 mmol) of 1,8-bis-dimethylaminonaphthalene in 40 ml of dichloromethane was heated to reflux for 6 hr. The mixture was then cooled to ambient temperature and concentrated under vacuum. The residue was dissolved in diethyl ether and was washed twice with 10% aqueous sodium hydrogen sulfate and once with saturated aqueous sodium bicarbonate. The organic layer was dried over magnesium sulfate, filtered and concentrated under vacuum. Preparative HPLC afforded 1.8 g (79%) of the desired intermediate, [α]D =-24.8° (c=1, dichloromethane).

Workup

  1. temperatureto reflux for 6 hr
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in diethyl ether
  4. washwas washed twice with 10% aqueous sodium hydrogen sulfate and once with saturated aqueous sodium bicarbonate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-16bab3178c4b4a79bf1e83aabf79ac1c
Source dataset
uspto-grants-1990_11
Patent number
US04968678

Reaction notes

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