Lithium Hydroxide → Glycine, N-[(2-oxo-2H-1-benzopyran-3-yl)carbonyl]-

HRID 2243838Notes

Reaction equation

HRID 2243838 reaction equation
C[O:2][C:3](=[O:19])[CH2:4][NH:5][C:6]([C:8]1[C:9](=[O:18])[O:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7].[Li+].[OH-]>C1COCC1.O>[O:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[C:8]([C:6]([NH:5][CH2:4][C:3]([OH:19])=[O:2])=[O:7])[C:9]1=[O:18]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 599285Coumarine 3-carboxamide, N-metoxycarbonylmethyl-

Product 1

HCID 12191927Glycine, N-[(2-oxo-2H-1-benzopyran-3-yl)carbonyl]-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of coumarin-3-carbonylamino-acetic acid methyl ester (312 mg, 1.19 mmol), in THF (12 ml) under Ar atmosphere, at 0° C. (ice bath), a solution of LiOH in H2O (0.2 M) was added dropwise. The reaction mixture was stirred vigorously at room temperature until total conversion was observed by TLC (2 hours). The solution was partially concentrated and Et2O was added (10 ml). The organic layer was washed with NaHCO3 (10 ml, sat) and the combined aqueous layers were acidified with boo KHSO4 (pH=3-4) and extracted with ether (3×20 ml). The organic layer was concentrated at reduced pressure to afford 8G9C1 (280 mg, 95%) as a white solid.

Workup

  1. customwas observed by TLC (2 hours)
  2. concentrationThe solution was partially concentrated
  3. additionEt2O was added (10 ml)
  4. washThe organic layer was washed with NaHCO3 (10 ml, sat)
  5. extractionextracted with ether (3×20 ml)
  6. concentrationThe organic layer was concentrated at reduced pressure
  7. customto afford 8G9C1 (280 mg, 95%) as a white solid

Sources & evidence

ORD record
ord-a68ffa18722847efa6d56e1244b3c4de
Source dataset
uspto-grants-2010_03
Patent number
US07678765B2

Reaction notes

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