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

HRID 1394006Notes

Reaction equation

HRID 1394006 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 aquous layers were acidified with 10% 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-644b9337ca70425dae1f7c7632258036
Source dataset
uspto-grants-2008_03
Patent number
US07348310B2

Reaction notes

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