Hydrochloric Acid → [(1-Benzyl-4-hydroxy-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine-5-carbonyl)-amino]-acetic acid

HRID 642245Notes

Reaction equation

HRID 642245 reaction equation
C(O[C:4]([C:6]1[C:7]([O:24]C(=O)C(C)(C)C)=[C:8]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])C.C[O-].[Na+].Cl.[NH2:35][CH2:36][C:37]([OH:39])=[O:38]>CO>[CH2:17]([N:12]1[C:9]2=[CH:10][N:11]=[C:6]([C:4]([NH:35][CH2:36][C:37]([OH:39])=[O:38])=[O:5])[C:7]([OH:24])=[C:8]2[C:14]([CH3:15])=[C:13]1[CH3:16])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 10942334Sodium Methoxide2×HCID 684277091-benzyl-4-(2,2-dimethyl-propionyloxy)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 24756720[(1-Benzyl-4-hydroxy-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine-5-carbonyl)-amino]-acetic acidYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
60 °C

Procedure

A mixture of 1-benzyl-4-(2,2-dimethyl-propionyloxy)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (70 mg, 0.171 mmol), NaOMe in MeOH (1.02 mL, 0.51 mmol, 0.5 M), and methanol (3 mL) was stirred overnight at 60° C.; then the reaction was cooled to room temperature and acidified to pH=6 with 2 M HCl aqueous solution. The solvents were then removed, and the residue was oil pumped to dryness. The left residue was then refluxed with glycine (257 mg, 3.42 mmol), NaOMe in MeOH (5.13 mL, 2.57 mmol, 0.5 M) overnight; the solvent was removed, the residue was dissolved in water and then extracted once with MTBE, the aqueous layer was acidified with HCl (2 M) aqueous solution to pH=1-2; the precipitated solids were collected by filtration, washed briefly with water and freeze-dried to give powder, the desired title compound (53 mg, 88%); ESI MS (m/z): 354 (M+H+).

Workup

  1. temperaturethen the reaction was cooled to room temperature
  2. customThe solvents were then removed
  3. customthe solvent was removed
  4. dissolutionthe residue was dissolved in water
  5. extractionextracted once with MTBE
  6. filtrationthe precipitated solids were collected by filtration
  7. washwashed briefly with water
  8. customfreeze-dried
  9. customto give powder

Sources & evidence

ORD record
ord-74e21043afa048a4a1a1035855499a4d
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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