Ammonia → HCID 13388560, compound

HRID 978228Notes

Reaction equation

HRID 978228 reaction equation
[CH2:1]1[O:6][C:4](=[O:5])[C@H:3]([OH:7])[C@H:2]1[OH:8].[NH3:9]>CO>[O:5]=[C:4]([NH2:9])[C@@H:3]([C@H:2]([CH2:1][OH:6])[OH:8])[OH:7]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 2724794(3R,4S)-3,4-dihydroxydihydrofuran-2(3H)-one

Product 1

HCID 13388560HCID 13388560, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5.50 g (46.57 mmoles) L-threonolactone in 100 mL MeOH, previously saturated with anhydrous NH3 at 0° C., was kept at room temperature for 48 h in a pressure bottle. The solvent was evaporated in vacuo, the residual oil re-evaporated from absolute EtOH, and the resulting solid crystallized from boiling EtOH. The crystals were collected after cooling at 0° C., washed with EtOH-Et2O (1:1 parts by volume), then with Et2O, and dried at 40° C./0.005 mm Hg to give 6.023 g (95.7%) of analytically pure product L-threonamide, m.p. 105°-107° C.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residual oil re-evaporated from absolute EtOH
  3. customthe resulting solid crystallized
  4. customThe crystals were collected
  5. washwashed with EtOH-Et2O (1:1 parts by volume)
  6. dry with materialwith Et2O, and dried at 40° C./0.005 mm Hg

Sources & evidence

ORD record
ord-53d8b9a0d56d4064bd3e00364ed5dd3a
Source dataset
uspto-grants-1987_05
Patent number
US04663469

Reaction notes

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