Ethyl bromopyruvate → N-[4-(Ethoxycarbonyl)-1,3-thiazol-2-yl]hexopyranosylamine--hydrogen bromide (1/1)

HRID 1163877Notes

Reaction equation

HRID 1163877 reaction equation
[Br:1][CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C@@H:10]1([NH:21][C:22]([NH2:24])=[S:23])[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]([OH:14])[C@H:11]1[OH:12]>C(O)C>[BrH:1].[C@@H:10]1([NH:21][C:22]2[S:23][CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:24]=2)[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]([OH:14])[C@H:11]1[OH:12]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 2728946Thiourea, beta-D-glucopyranosyl-

Product 1

HCID 157591N-[4-(Ethoxycarbonyl)-1,3-thiazol-2-yl]hexopyranosylamine--hydrogen bromide (1/1)

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl bromopyruvate (8.99 g., 0.047 mole) was added to a suspension of N-β-D-glucopyranosylthiourea (10 g., 0.042 mole) in 120 ml. of hot ethanol, and the reaction was completed by heating 30 minutes. During the heating, the mixture became a clear solution. The reaction solution was evaporated to dryness in vacuo. The residue was crystallized from ethanol and acetone, filtered, and dried at room temperature in vacuo, yielding 16.03 g. (91.9%); white powder; m.p. 162°-163°(dec.).

Workup

  1. temperatureby heating 30 minutes
  2. customThe reaction solution was evaporated to dryness in vacuo
  3. customThe residue was crystallized from ethanol and acetone
  4. filtrationfiltered
  5. customdried at room temperature in vacuo
  6. customyielding 16.03 g

Sources & evidence

ORD record
ord-7eca43226cbf4680be77ee7ecbcefe63
Source dataset
uspto-grants-1983_01
Patent number
US04367226

Reaction notes

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