Water → HCID 18608587, compound

HRID 2119156Notes

Reaction equation

HRID 2119156 reaction equation
[C:1](Cl)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Cl.[OH:16][CH:17]1[O:25][C@H:24]([CH2:26][OH:27])[C@@H:22]([OH:23])[C@H:20]([OH:21])[C@H:18]1[NH2:19].O>O1CCCC1.C(=O)([O-])[O-].[Na+].[Na+]>[C:1]([NH:19][C@@H:18]1[C@@H:20]([OH:21])[C@H:22]([OH:23])[C@@H:24]([CH2:26][OH:27])[O:25][CH:17]1[OH:16])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 962WaterHCID 8166Dodecanoyl chlorideHCID 2723635(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride

Product 1

HCID 18608587HCID 18608587, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 10340Sodium CarbonateSolvent

Procedure

55 g of dodecanoyl chloride were dissolved in 170 ml of tetrahydrofuran and added dropwise, with vigorous stirring, to a solution of 54 g of D-glucosamine hydrochloride in 330 ml of aqueous sodium carbonate solution (20%). After completion of the addition of the acid chloride, the mixture was stirred for a further hour, then 500 ml of water were added to the batch and the solid material was filtered off with suction and washed with water. The residue was recrystallised from isopropanol/water 10/1 (v/v) and dried under high vacuum.

Workup

  1. filtrationthe solid material was filtered off with suction
  2. washwashed with water
  3. customThe residue was recrystallised from isopropanol/water 10/1 (v/v)
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-e7a568efb7824d31bdf0596d6b8d1bc8
Source dataset
uspto-grants-1987_07
Patent number
US04683222

Reaction notes

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