Diisopropylethylamine → HCID 102326821, compound
Reaction equation
[CH3:1][C:2]([CH3:29])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:28])=[CH:7]/[CH2:8][CH2:9][C@:10]1([CH3:27])[O:19][C:18]2[C:13](=[C:14]([OH:25])[CH:15]=[C:16]3[C:22](=[O:23])[N:21]([CH3:24])[CH2:20][C:17]3=2)[CH2:12][C@@H:11]1[OH:26].C(N(CC)C(C)C)(C)C.C[Si](C=[N+]=[N-])(C)C>C(#N)C>[CH3:18][O:19][CH3:10].[CH3:1][C:2]([CH3:29])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:28])=[CH:7]/[CH2:8][CH2:9][C@:10]1([CH3:27])[O:19][C:18]2[C:13](=[C:14]([OH:25])[CH:15]=[C:16]3[C:22](=[O:23])[N:21]([CH3:24])[CH2:20][C:17]3=2)[CH2:12][C@@H:11]1[OH:26]Participants
Procedure
SMTP-0 (50 mg, 78 μmol) was dissolved in acetonitrile (2 mL), and N,N-diisopropylethylamine (50 μl) and trimethylsilyldiazomethane (2.0 M, hexane solution) (150 μl) were added thereto. The mixture was stirred for 24 hours at room temperature. The reaction liquid was concentrated to obtain methyl ether of SMTP-0 (SMTP-0-OMe) (44 mg). SMTP-0-OMe (20 mg, 50 μmol) was dissolved in N,N-dimethylformamide (1 mL), and R-(−)-α-methoxy-α-(trifluoromethyl)phenylacetyl chloride (25 mg), triethylamine (30 μl) and 4-dimethylaminopyridine (2 mg) were added thereto. The mixture was stirred for 24 hours at room temperature. Water (10 mL) was added to the reaction liquid, and the mixture was extracted with ethyl acetate (50 mL). The organic layer was washed with 1 N HCl, a saturated aqueous solution of sodium hydrogen carbonate and saturated brine, then dried using anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by thin layer chromatography (hexane-ethyl acetate), to obtain SMTP-0-OMe ester of S-α-methoxy-α-(trifluoromethyl)phenylacetylacetic acid (S-MTPA-SMTP-0-OMe) (18 mg).
Workup
- customThe reaction liquid
- concentrationwas concentrated
Sources & evidence
- ORD record
- ord-444ecb39d67a414789a1b03c9dd10829
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08110596B2
Reaction notes
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