Pyridine → HCID 70196286, compound

HRID 649805Notes

Reaction equation

HRID 649805 reaction equation
[C:1]([O:9][C@H:10]1[CH2:15][C@@H:14]([CH2:16][N:17]2[C:21](=[O:22])[C:20]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]3[C:18]2=[O:27])[O:13][C@@H:12]([N:28]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29]2)[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.O[N:44]1[C:48](=O)C[CH2:46][C:45]1=[O:50].[N:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>ClCCl.O1CCCC1>[C:1]([O:9][C@H:10]1[CH2:15][C@@H:14]([CH2:16][N:17]2[C:21](=[O:22])[C:20]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]3[C:18]2=[O:27])[O:13][C@@H:12]([N:28]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]([C:46]3[C:45](=[O:50])[NH:44][C:48]4[C:56]([N:51]=3)=[CH:55][CH:54]=[CH:53][CH:52]=4)=[CH:29]2)[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 80170N-HydroxysuccinimideHCID 70197951HCID 70197951, compound

Product 1

HCID 70196286HCID 70196286, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1(3-O-Benzoyl-6-phthalimido-2,4,6-trideoxy-β-D-threo-hexopyranosyl)-1H-indole (0.30 g, 0.62 mmol) was dissolved in dichloromethane (3 ml) and cooled to 0° C. Oxalyichloride (65 μl, 0.74 mmol) was added and the reaction mixture kept at 0° C. for 15 ml and then stirred at room temperature for another 45 minutes. N-hydroxysuccinimid (0.08 g 0.70 mmol) was added followed by careful addition of pyridine (0.10 ml, 1.23 mmol). The reaction mixture was stirred at room temperature for 16 hours and then washed twice with water. The organic layer was evaporated and the crude mixed with tetrahydrofuran (10 ml) and 1,2-diphenylenediamine (0.09 g, 0.80 mmol) and stirred at room temperature for 16 hours. The resulting percipitate was collected by centrifugation, washed twice with ether and dried to give 0.12 g (32%) of the subtitle product.

Workup

  1. customkept at 0° C. for 15 ml
  2. stirringThe reaction mixture was stirred at room temperature for 16 hours
  3. washwashed twice with water
  4. customThe organic layer was evaporated
  5. stirringstirred at room temperature for 16 hours
  6. customThe resulting percipitate was collected by centrifugation
  7. washwashed twice with ether
  8. customdried

Sources & evidence

ORD record
ord-c961dcb8c0d543abbaee250e81040067
Source dataset
uspto-grants-2001_08
Patent number
US06271231B1

Reaction notes

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