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

HRID 642415Notes

Reaction equation

HRID 642415 reaction equation
C(O[C:4]([C:6]1[C:7]([O:23]C(=O)C(C)(C)C)=[C:8]2[C:14]([Cl:15])=[CH:13][N:12]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])C.C[O-].[Na+].CO.[NH2:35][CH2:36][C:37]([OH:39])=[O:38]>>[CH2:16]([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:23])=[C:8]2[C:14]([Cl:15])=[CH:13]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 750GlycineHCID 23694274Sodium methanolate methanol2×HCID 684289301-Benzyl-3-chloro-4-(2,2-dimethyl-propionyloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 68428596[(1-Benzyl-3-chloro-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carbonyl)-amino]-acetic acidYield 47.9%

Procedure

A mixture of 1-benzyl-3-chloro-4-(2,2-dimethyl-propionyloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (65 mg) and NaOMe/HOMe (0.94 mL, 0.5 M) was refluxed for 1 h; then cooled, partitioned between EtOAc and diluted HCl solution, organic phase was washed with sat. NaCl solution, dried over sodium sulfate and then filtered, concentrated to give a residue, which was refluxed with glycine (236 mg) and NaOMe/HOMe (4.71 mL) overnight; the solvent was subsequently removed, the residue was partitioned between MTBE (methyl tert-butyl ether) and water, the aqueous phase was then acidified with 2 M HCl to pH=1-2, the solids were collected with filtration after cooled in an ice/water bath, the solids were then freeze dried to give the title compound (27 mg). ESI (m/z): 360 (M+H)+.

Workup

  1. temperaturewas refluxed for 1 h
  2. temperaturethen cooled
  3. custompartitioned between EtOAc and diluted HCl solution, organic phase
  4. washwas washed with sat. NaCl solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a residue, which
  9. customthe solvent was subsequently removed
  10. customthe residue was partitioned between MTBE (methyl tert-butyl ether) and water
  11. filtrationthe solids were collected with filtration
  12. temperatureafter cooled in an ice/water bath
  13. customthe solids were then freeze dried

Sources & evidence

ORD record
ord-00585427fb97462ea69fd920c4c25920
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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