Aluminum → HCID 69624706, compound

HRID 397289Notes

Reaction equation

HRID 397289 reaction equation
[CH2:1]([O:3][C:4](=[O:57])[C:5](=[N:55]O)[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[C@H:16]1[O:45][C@H:44]([CH2:46][O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C@@H:35]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@H:26]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C@@H:17]1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:2].[Al]>O1CCCC1.O>[CH2:1]([O:3][C:4](=[O:57])[CH:5]([NH2:55])[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[C@H:16]1[O:45][C@H:44]([CH2:46][O:47][CH2:48][C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[C@@H:35]([O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C@H:26]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C@@H:17]1[O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH3:2]

Participants

5

Reactant 2

HCID 5359268AluminumHCID 86759126HCID 86759126, compound

Product 1

HCID 69624706HCID 69624706, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

First, 1.73 g (2.25 mmol) of 2-hydroxyimino-3-[2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)indole-3-yl]propionic acid ethyl ester [compound (IX) wherein R1 to R4 are benzyl and R6 is ethyl] was dissolved in tetrahydrofuran (225 ml)-water (25 ml). Then, aluminum amalgam prepared from 8.50 g (0.32 mmol) of aluminum was added to the mixture and stirred at 55° C. for about 0.5 hour. Then, the reacted solution was filtrated on Celite which was then washed with 10% ethanol-dichloromethane. The filtrate was then concentrated and the residue was fractionated by column chromatography on silica gel [silica gel: Merck Kieselgel 60 (230-400 mesh ASTM); elution solvent: 3% methanol-dichloromethane] to give 1.54 g (yield 90%) of 2-amino-3-[2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)indole-3-yl]propionic acid ethyl ester [compound (x) wherein R1 to R4 are benzyl and R6 is ethyl].

Workup

  1. additionwas added to the mixture
  2. filtrationThen, the reacted solution was filtrated on Celite which
  3. washwas then washed with 10% ethanol-dichloromethane
  4. concentrationThe filtrate was then concentrated

Sources & evidence

ORD record
ord-d81857a41da14bd5bfb648b97ec7cf19
Source dataset
uspto-grants-2003_08
Patent number
US06610502B1

Reaction notes

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