Carbonate Ion → HCID 22811340, compound

HRID 1706840Notes

Reaction equation

HRID 1706840 reaction equation
[C:1]([NH:4][CH2:5][C@H:6]1[O:13][C@H:10]([O:11]C)[CH2:9][CH2:8][C@@H:7]1[OH:14])(=[O:3])[CH3:2].C(=O)([O-])[O-]>Cl>[C:1]([NH:4][CH2:5][C@H:6]1[O:13][CH:10]([OH:11])[CH2:9][CH2:8][C@@H:7]1[OH:14])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 19660Carbonate IonHCID 70583977HCID 70583977, compound

Product 1

HCID 22811340HCID 22811340, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Methyl 6-acetamido-2,3,6-trideoxy-α-D-erythro-hexopyranoside (1.5 g) in 0.1 M aqueous hydrochloric acid (30 ml) was heated at 100° for 0.5 h. The solution was neutralized with Amberlite IR-400 (carbonate form) resin and evaporated in vacuo to yield a syrup, 1.46 g. This syrup showed the presence of two compounds by TLC (ether-methanol, 9:1): (a) Rf 0.08 and (b) Rf 0.05. The separation of these two components was achieved by chromatography in a silica-gel column using mixtures of ether-methanol as eluants. Compound (a), 6-acetamido-2,3,6-trideoxy-D-erythro hexopyranose (Rf 0.08) was obtained as a colourless syrup (0.75 g, 50%) which reduced Fehling's reagent. [α]546125 +50°, [α]D25 +36° (c 0.5, water).

Workup

  1. customevaporated in vacuo
  2. customto yield a syrup, 1.46 g
  3. customThe separation of these two components

Sources & evidence

ORD record
ord-1988997cd817407f8f55d71ea004699c
Source dataset
uspto-grants-1980_06
Patent number
US04208531

Reaction notes

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