Hydrochloric Acid → [[2-(methylthio)-5-(aminooxoacetyl)-6-ethyl-7-([1,1'-biphenyl]-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid

HRID 1934440Notes

Reaction equation

HRID 1934440 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][O:5][C:6]1[C:7]2[C:16]([C:17](=[O:21])[C:18]([NH2:20])=[O:19])=[C:15]([CH2:22][CH3:23])[N:14]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:8]=2[N:9]=[C:10]([S:12][CH3:13])[N:11]=1.[OH-].[Na+].Cl>CO>[CH3:13][S:12][C:10]1[N:11]=[C:6]([O:5][CH2:4][C:3]([OH:37])=[O:2])[C:7]2[C:16]([C:17](=[O:21])[C:18]([NH2:20])=[O:19])=[C:15]([CH2:22][CH3:23])[N:14]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:8]=2[N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69557498HCID 69557498, compound

Product 1

HCID 69557799[[2-(methylthio)-5-(aminooxoacetyl)-6-ethyl-7-([1,1'-biphenyl]-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acidYield 69.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 240 mg (0.462 mmol) of [[2-(methylthio)-5-(aminooxoacetyl)-6-ethyl-7-([1,1′-biphenyl]-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester and 15 mL of methanol was treated with 0.35 mL of 2 M sodium hydroxide and stirred at ambient temperature for 24 hours. The reaction was then adjusted to pH 2 by the addition of 1 M HCl. The mixture was concentrated and the solids were dried in vacuo to provide 162 mg (69%) of [[2-(methylthio)-5-(aminooxoacetyl)-6-ethyl-7-([1,1 ′-biphenyl] -2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid as a solid. nmr (300 MHz, dmso-d6) δ0.78 (t, 3H), 2.44 (s, 3H), 2.60 (q, 2H), 4.84 (s, 2H), 5.40 (s, 2H), 6.74 (d, 1H), 7.2-7.5 (m, 9H), 7.60 (s, 1H), 7.97 (s, 1H)

Workup

  1. concentrationThe mixture was concentrated
  2. customthe solids were dried in vacuo

Sources & evidence

ORD record
ord-f850e6a542d54608bbf245fde9a69115
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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