Sodium Carbonate Monohydrate → Alpha Bromolauroyl-lactosamine

HRID 343753Notes

Reaction equation

HRID 343753 reaction equation
[Br:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:3](Cl)=[O:4].[OH:16][CH:17]1[O:36][C@H:35]([CH2:37][OH:38])[C@@H:22]([O:23][C@@H:24]2[O:32][C@H:31]([CH2:33][OH:34])[C@H:29]([OH:30])[C@H:27]([OH:28])[C@H:25]2[OH:26])[C@H:20]([OH:21])[C@H:18]1[NH2:19].O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC>[Br:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:3]([C:17]1([O:36][C@H:35]([CH2:37][OH:38])[C@@H:22]([O:23][C@@H:24]2[O:32][C@H:31]([CH2:33][OH:34])[C@H:29]([OH:30])[C@H:27]([OH:28])[C@H:25]2[OH:26])[C@H:20]([OH:21])[C@H:18]1[NH2:19])[OH:16])=[O:4]

Participants

5

Reactant 3

HCID 2735133Sodium Carbonate MonohydrateHCID 114732932-Amino-2-deoxy-4-O-beta-D-galactopyranosyl-D-glucoseHCID 155187952-Bromododecanoyl chloride

Product 1

HCID 131721089Alpha Bromolauroyl-lactosamine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Alpha-bromolauroyl chloride (0.50 g) was added drop-wise to a 30% aqueous solution of lactosamine (0.7 g) at zero degrees centigrade. The pH of the solution was kept above 9.0 by adding saturated sodium carbonate water solution. The reaction was stirred overnight at room temperature. It was then heated to 36° C. for an additional hour. The final product was obtained by extraction two times with n-butanol. After evaporating butanol, the remaining solid material was washed with cold ethanol. The final product was collected by filtration. The NMR spectra showed that the solid material is the expected product. The yield of the reaction was 75%.

Workup

  1. temperatureIt was then heated to 36° C. for an additional hour

Sources & evidence

ORD record
ord-5c4cb051124d42eabf3f2ce1312b2ed5
Source dataset
uspto-grants-1999_01
Patent number
US05863886

Reaction notes

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