Nadide (JAN/USAN/INN) → HCID 86745689, compound

HRID 1030460Notes

Reaction equation

HRID 1030460 reaction equation
[CH:1]1[CH:6]=[N+:5]([C@@H:7]2[O:11][C@H:10]([CH2:12][O:13][P:14]([O:17][P:18]([O:21][CH2:22][C@H:23]3[O:27][C@@H:26]([N:28]4[C:32]5[N:33]=[CH:34][N:35]=[C:36]([NH2:37])[C:31]=5[N:30]=[CH:29]4)[C@H:25]([OH:38])[C@@H:24]3[OH:39])([OH:20])=[O:19])([OH:16])=[O:15])[C@@H:9]([OH:40])[C@H:8]2[OH:41])[CH:4]=[C:3]([C:42]([NH2:44])=[O:43])[CH:2]=1.C(Cl)([Cl:47])=S.[C:49](=[O:52])([O-])[O-].[Na+].[Na+]>O.C(Cl)(Cl)Cl>[CH:34]1[N:35]=[C:36]([NH2:37])[C:31]2[N:30]=[CH:29][N:28]([C@@H:26]3[O:27][C@H:23]([CH2:22][O:21][P:18]([O:17][P:14]([O:13][CH2:12][C@H:10]4[O:11][C@@H:7]([N:5]5[CH:4]=[C:3]([C:42]([NH2:44])=[O:43])[CH2:2][CH:1]=[CH:6]5)[C@H:8]([OH:41])[C@@H:9]4[OH:40])([OH:16])=[O:15])([OH:20])=[O:19])[C@@H:24]([OH:39])[C@H:25]3[OH:38])[C:32]=2[N:33]=1.[CH2:2]1[C:49](=[O:52])[N:44]([Cl:47])[C:42](=[O:43])[CH2:3]1

Participants

6

Reactant 3

HCID 5893Nadide (JAN/USAN/INN)HCID 10040ThiophosgeneHCID 10340Sodium Carbonate

Product 1

HCID 86745689HCID 86745689, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

2 mmol of NAD+ were dissolved in 10 ml of H2O in a round-bottomed flask with attached bubble-counter, and a little Na2CO3 was added. A solution of 20 mmol of thiophosgene in 10 ml of CHCl3 was added with vigorous stirring at 20° C. The pH was checked every 10 minutes and kept between 5.5 and 8.5 by the addition of small amounts of sodium carbonate. After 3.5 hours there was no longer any change in the pH, and no further gas was evolved. The mixture was evaporated to dryness in vacuo and freeze-dried. The slightly brownish product mixture could be purified of by-products by column chromatography on silica gel using water/acetonitrile as eluent. However, it is advisable to use the product mixture unpurified for the reaction with the polymer (see Example 2), since purification by ultrafiltration of the product immobilized on the polymer is considerably more straightforward and, moreover, the sensitivity of NAD-NCS results in losses due to dimerization and trimerization during purification.

Workup

  1. customwith attached bubble-counter
  2. additiona little Na2CO3 was added
  3. waitAfter 3.5 hours there was no longer
  4. customThe mixture was evaporated to dryness in vacuo
  5. customfreeze-dried
  6. customThe slightly brownish product mixture could be purified of by-products by column chromatography on silica gel
  7. customunpurified for the reaction with the polymer (see Example 2)
  8. filtrationsince purification by ultrafiltration of the product

Sources & evidence

ORD record
ord-0cc00ff483724b29b125cfea4b2b4c6f
Source dataset
uspto-grants-1992_04
Patent number
US05106740

Reaction notes

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