2,4,6-Trimethylpyridine → HCID 54065624, compound
Reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:17]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@@H:16]([OH:26])[C@@H:15]([CH2:27][O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:14][C@H:10]1[S:11][CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C(C)=CC(C)=CC=1C.[Br:45][CH2:46][C:47](Br)=[O:48]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([O:8][C@@H:9]1[C@@H:17]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C@@:16]([C:47](=[O:48])[CH2:46][Br:45])([OH:26])[C@@H:15]([CH2:27][O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[O:14][C@H:10]1[S:11][CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
6
Procedure
A mixture of ethyl 2,3,6-tri-O-benzyl-1-thio-β-D-galactopyranoside (4.14 g, 8.38 mmol), sym. collidine (3.65 g, 30.16 mmol), and 4-dimethylaminopyridine in dry CH2Cl2 (60 ml) was stirred at 0° C. and bromoacetyl bromide (2.53, 2.57 mmol) in CH2Cl2 added dropwise in 15 minutes. The reaction mixture was diluted with CH2Cl2 (100 ml) and washed with 5% HCl solution (3×30 ml) and saturated NaHCO3 solution (30 ml). The solution was dried over MgSO4 and evaporated. The residue was purified by chromatography using hexane/EtOAc 2:1 as the mobile phase to give ethyl 2,3,6-tri-O-benzyl-4-bromoacetyl-1-thio-β-D-galactopyranoside (4.84 g, 94%)
Workup
- washwashed with 5% HCl solution (3×30 ml) and saturated NaHCO3 solution (30 ml)
- dry with materialThe solution was dried over MgSO4
- customevaporated
- customThe residue was purified by chromatography
Sources & evidence
- ORD record
- ord-1f68852e43b041b18553bfff2448a6fb
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06723843B2
Reaction notes
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