Sodium Carbonate → Alpha Bromo-N-Methyl-lauroyl lactosamine

HRID 343754Notes

Reaction equation

HRID 343754 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].[CH3:16][NH:17][C@@H:18]1[C@@H:24]([OH:25])[C@H:23]([O:26][C@@H:27]2[O:35][C@H:34]([CH2:36][OH:37])[C@H:32]([OH:33])[C@H:30]([OH:31])[C@H:28]2[OH:29])[C@@H:22]([CH2:38][OH:39])[O:21][CH:19]1[OH:20].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:19]1([O:21][C@H:22]([CH2:38][OH:39])[C@@H:23]([O:26][C@@H:27]2[O:35][C@H:34]([CH2:36][OH:37])[C@H:32]([OH:33])[C@H:30]([OH:31])[C@H:28]2[OH:29])[C@H:24]([OH:25])[C@H:18]1[NH:17][CH3:16])[OH:20])=[O:4]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 155187952-Bromododecanoyl chlorideHCID 101032338GlyTouCan:G87337FD

Product 1

HCID 131721090Alpha Bromo-N-Methyl-lauroyl lactosamine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Alpha-bromolauroyl chloride (2.4 g) was added drop-wise to a 30% aqueous solution of N-methyl-lactosamine (3.5 g) at zero degrees centigrade. The pH of the solution was maintained above 9 by the addition of a saturated aqueous sodium carbonate solution. The reaction was stirred overnight at room temperature. It was then heated up to 36° C. for an additional hour. The final product was obtained by extraction two times with n-butanol. The organic layer was dried with sodium sulfate and then rotevaporated under vacuum. The final product was taken for NMR analysis. The result confirmed that the solid material is the expected product. The yield of reaction was 80%.

Workup

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

Sources & evidence

ORD record
ord-1dee05548341430880ea248df145be0d
Source dataset
uspto-grants-1999_01
Patent number
US05863886

Reaction notes

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