Sodium Carbonate → (2,3,4,5,6-pentahydroxy-hexyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

HRID 2075643Notes

Reaction equation

HRID 2075643 reaction equation
[NH2:1][CH2:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[C:13](=[O:16])([O-])[O-:14].[Na+].[Na+].C(=O)([O-])ON1C(=O)CC([CH2:27][CH:28]2[C:40]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:34]3[C:29]2=[CH:30][CH:31]=[CH:32][CH:33]=3)C1=O>COCCOC>[CH:30]1[C:29]2[CH:28]([CH2:27][O:14][C:13](=[O:16])[NH:1][CH2:2][CH:3]([OH:4])[CH:5]([OH:6])[CH:7]([OH:8])[CH:9]([OH:10])[CH2:11][OH:12])[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34]=2[CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 452501Glucamine2×HCID 71304114(9H-fluoren-9-yl)methyl-2,5-dioxopyrrolidin-1-yl carbonate

Product 1

HCID 23132532(2,3,4,5,6-pentahydroxy-hexyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

D-glucamine (Compound 34: 9.0 g, 49.7 mmol) was mixed with 200 ml of a 10% aqueous solution of sodium carbonate, and this was followed by stirring under ice cooling. 9-Fluorenylmethylsuccinimidyl carbonate (16.7 g, 49.7 mmol) was dissolved in 200 ml of DME (1,2-dimethoxyethane) and added to the reaction system, and this was followed by stirring under ice cooling for 30 minutes. The precipitating crystal was collected by filtration and washed with H2O×3 and MeOH×3. The crystal was dried under reduced pressure to yield the desired compound (2,3,4,5,6-pentahydroxy-hexyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (Compound 35: 20 g) quantitatively.

Workup

  1. additionadded to the reaction system
  2. stirringby stirring under ice cooling for 30 minutes
  3. filtrationThe precipitating crystal was collected by filtration
  4. washwashed with H2O×3 and MeOH×3
  5. customThe crystal was dried under reduced pressure

Sources & evidence

ORD record
ord-c8ae21fe0735404097a30b78dd48259d
Source dataset
uspto-grants-2011_04
Patent number
US07919653B2

Reaction notes

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