L-Alanine → HCID 69516518, compound

HRID 853815Notes

Reaction equation

HRID 853815 reaction equation
[O:1]=[C:2]1[NH:6][CH2:5][C:4](=[O:7])[N:3]1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]#[N:19])=[CH:10][CH:9]=1.N[C@H](C(O)=O)C.C([O-])([O-])=O.[Na+].[Na+].[CH:32](=O)[C:33]1[C:34](=[CH:36][CH:37]=[CH:38][CH:39]=1)[OH:35]>O>[OH:35][C:34]1[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=1[CH:32]=[C:5]1[C:4](=[O:7])[N:3]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]#[N:19])=[CH:10][CH:9]=2)[C:2](=[O:1])[NH:6]1

Participants

6

Reactant 4

HCID 5950L-AlanineHCID 6998SalicylaldehydeHCID 10340Sodium CarbonateHCID 58932670HCID 58932670, compound

Product 1

HCID 69516518HCID 69516518, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of compound 1C (150 mg, 0.6 mmol), alanine (53.1 mg, 0.6 mmol), and Na2CO3 (31.7 mg, 0.3 mmol) in water (1.4 mL) was treated with salicylaldehyde (0.11 mL, 0.94 mmol) and refluxed for 3.0 h. (Ref: Eur. J. Org. Chem. 1999, 2609-2621). The mixture was diluted with water (1 mL) and filtered, washing the yellow precipitates with water (2×2 mL). The yellow solids were triturated with ether (2 mL) and dried to give the title compound as a yellow solid (74.9 mg, 35.4%), mp 251-252° C. LC/MS m/z 356 [M+H]+.

Workup

  1. temperaturerefluxed for 3.0 h. (Ref: Eur. J. Org. Chem. 1999, 2609-2621)
  2. filtrationfiltered
  3. washwashing the
  4. customyellow precipitates with water (2×2 mL)
  5. customThe yellow solids were triturated with ether (2 mL)
  6. customdried

Sources & evidence

ORD record
ord-8a2acac0d5394cdaa30a19e1bb4a642f
Source dataset
uspto-grants-2007_08
Patent number
US07256208B2

Reaction notes

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