Glycine → HCID 24757245, compound

HRID 642335Notes

Reaction equation

HRID 642335 reaction equation
C(O[C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][CH:16]=3)[S:14][C:8]=2[C:7]=1[OH:28])=[O:5])C.[NH2:29][CH2:30][C:31]([OH:33])=[O:32]>C[O-].[Na+].CO>[OH:28][C:7]1[C:8]2[S:14][C:13]([C:15]3[CH:16]=[CH:17][C:18]([O:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)=[CH:19][CH:20]=3)=[N:12][C:9]=2[CH:10]=[N:11][C:6]=1[C:4]([NH:29][CH2:30][C:31]([OH:33])=[O:32])=[O:5]

Participants

4

Reactant 2

HCID 750GlycineHCID 68426536HCID 68426536, compound

Product 1

HCID 24757245HCID 24757245, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 7-hydroxy-2-(4-phenoxy-phenyl)-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (75 mg, 0.19 mmole) and glycine (286 mg, 3.81 mmole) in 0.5 M sodium methoxide/methanol (7.2 ml) was refluxed for three days before it was cooled to room temperature and concentrated in vacuo. Water (75 ml) was added and pH was adjusted to 10 with 1N HCl (2 ml). The mixture was extracted with methyl tert-butyl ether (2×30 ml) and dichloromethane (30 ml). The remaining aqueous layer was acidified to pH=3 with 1N HCl (3 ml). The solid precipitate was filtered, washed with water and dried in vacuo to give the title compound as a white solid (55 mg). 1H NMR (DMSO-d6, 200 MHz): δ=9.45 (br s, 1H), 8.87 (s, 1H), 8.17 (m, 2H), 7.47 (m, 2H), 7.17 (m, 5H), 4.03 (d, J=6.3 Hz, 2H); MS: (+) m/z 421.07 (M+1). (−) m/z 419.87 (M−1).

Workup

  1. temperaturewas refluxed for three days before it
  2. concentrationconcentrated in vacuo
  3. additionWater (75 ml) was added
  4. extractionThe mixture was extracted with methyl tert-butyl ether (2×30 ml) and dichloromethane (30 ml)
  5. filtrationThe solid precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-decd90c7cb794d20ab7ef91b734e3a04
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

Loading…