Formaldehyde → t-butyl hydroxymethylacrylate
Reaction equation
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[CH:2]=[CH2:3].[CH2:10]=[O:11].N12CCC(CC1)C(O)C2>>[OH:11][CH2:10][C:2](=[CH2:3])[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]Participants
Procedure
In a typical procedure, t-butyl acrylate (III) is reacted with paraformaldehyde in the presence of 3-quinuclidinol to provide t-butyl hydroxymethylacrylate (IV). This is first treated with thionyl chloride in the presence of triethylamine and pyridine to provide the corresponding chloromethylacrylate, which is then reacted with (S,S)-α-α′-dimethyldibenzylamine to provide an acrylate of the formula (V). This is converted to a compound of the formula (IX) by the method set out in Tet. Lett., 1993, 34(8), 1323-6. A compound of the formula (IX) is then condensed with a lysine derivative of the formula (X) by a similar procedure to that described in EP-A-0358398 for the preparation of a compound of the formula (XI). A compound of the formula (XI) is then converted to a compound of the formula (II) using a solution of trifluoroacetic acid and anisole in dichloromethane.
Sources & evidence
- ORD record
- ord-f3ea0203577249fe941e129b7d21ab28
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06180665B2
Reaction notes
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