(RS)-3-[5-(tetrahydro-pyran-2-yloxymethyl)-isoxazol-3-yl]-benzoic acid methyl ester → (RS)-3-Oxo-3-{3-[5-(tetrahydro-pyran-2-yloxymethyl)-isoxazol-3-yl]-phenyl}-propionic acid tert.-butyl ester
Reaction equation
CO[C:3](=[O:23])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:14]=[C:13]([CH2:15][O:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[O:12][N:11]=2)[CH:5]=1.[C:24]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])(=[O:26])[CH3:25].[Li]>>[C:28]([O:27][C:24](=[O:26])[CH2:25][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:14]=[C:13]([CH2:15][O:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[O:12][N:11]=2)[CH:5]=1)([CH3:31])([CH3:30])[CH3:29]Participants
3
Procedure
The title compound was prepared from (RS)-3-[5-(tetrahydro-pyran-2-yloxymethyl)-isoxazol-3-yl]-benzoic acid methyl ester [prepared from (Z)-3-(hydroxyimino-methyl)-benzoic acid methyl ester [CAS-No. 91186-80-0] by treatment with NCS, cat. amount pyridine in CHCl3 followed by addition of (RS)-tetrahydro-2-(2-propynyloxy)-2H-pyran and slow addition of Et3N in CHCl3 at 23° C.] by treatment with lithium tert.-butyl acetate according to general procedure K (method b). Obtained as a yellow oil (3.00 g).
Sources & evidence
- ORD record
- ord-0aed13ab33754f7d9e32cb2e46fe4b59
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06548495B2
Reaction notes
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