benzyl 6-{bis[2-({2-[(alpha-L-fucopyranosyl)oxy]ethyl}amino)-2-oxoethyl]amino}-6-oxohexanoate → 6-{bis[2-({2-[(alpha-L-fucopyranosyl)oxy]ethyl}amino)-2-oxoethyl]amino}-6-oxohexanoic acid
Reaction equation
[C@@H:1]1([O:11][CH2:12][CH2:13][NH:14][C:15](=[O:51])[CH2:16][N:17]([CH2:34][C:35](=[O:50])[NH:36][CH2:37][CH2:38][O:39][C@@H:40]2[O:48][C@@H:47]([CH3:49])[C@@H:45]([OH:46])[C@@H:43]([OH:44])[C@@H:41]2[OH:42])[C:18](=[O:33])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]CC2C=CC=CC=2)=[O:24])[O:9][C@@H:8]([CH3:10])[C@@H:6]([OH:7])[C@@H:4]([OH:5])[C@@H:2]1[OH:3]>O.O[Pd]O>[C@@H:1]1([O:11][CH2:12][CH2:13][NH:14][C:15](=[O:51])[CH2:16][N:17]([CH2:34][C:35](=[O:50])[NH:36][CH2:37][CH2:38][O:39][C@@H:40]2[O:48][C@@H:47]([CH3:49])[C@@H:45]([OH:46])[C@@H:43]([OH:44])[C@@H:41]2[OH:42])[C:18](=[O:33])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[O:9][C@@H:8]([CH3:10])[C@@H:6]([OH:7])[C@@H:4]([OH:5])[C@@H:2]1[OH:3]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of benzyl 6-{bis[2-({2-[(α-L-fucopyranosyl)oxy]ethyl}amino)-2-oxoethyl]amino}-6-oxohexanoate (900 mg, 1.233 mmol) in H2O (5 mL) at rt was added dihydroxypalladium (866 mg, 1.233 mmol). The mixture was degassed and then stirred under a balloon of H2. After stirring at rt under H2 for 16 hr, the reaction mixture was filtered through a Celite pad and washed with CH3OH (3×10 mL). The filtrate was concentrated to give the title compound. LC-MS Method A: m/e=640.17 [M+1]; Rt=0.98 min.
Workup
- customThe mixture was degassed
- stirringAfter stirring at rt under H2 for 16 hr
- filtrationthe reaction mixture was filtered through a Celite pad
- washwashed with CH3OH (3×10 mL)
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-ee7cd11cb07a4846a5167efe2979e259
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09427475B2
Reaction notes
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