Hydrochloric Acid → HCID 69558269, compound

HRID 1934446Notes

Reaction equation

HRID 1934446 reaction equation
C[O:2][C:3](=[O:32])[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]=[C:27]([Cl:31])[CH:26]=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:32])=[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]=[C:27]([Cl:31])[CH:26]=3)[C:8]=2[N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69558667HCID 69558667, compound

Product 1

HCID 69558269HCID 69558269, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 109 mg (0.228 mmol) of [[2-(methylthio)-5-(aminooxoacetyl)-6-ethyl-7-[(3-chlorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester and 10 mL of methanol was treated with 0.17 mL of 2 M sodium hydroxide and stirred at reflux for 3 hours. The reaction was cooled to ambient temperature and neutralized to pH 1 with 1 M HCl then concentrated to a solid. The solids were triturated with water and dried in vacuo to provide 99 mg (94%) of [[2-(methylthio)-5-(aminooxoacetyl)-6-ethyl-7-[(3-chlorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid as a solid. nmr (300 MHz, dmso-d6) δ1.00 (t, 3H), 2.46 (s, 3H), 2.90 (q, 2H), 4.85 (s, 2H), 5.49 (s, 2H), 7.01 (m, 1H), 7.32 (m, 3H), 7.60 (s, 1H), 8.00 (s, 1H)

Workup

  1. temperatureat reflux for 3 hours
  2. concentrationthen concentrated to a solid
  3. customThe solids were triturated with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-9d1b275220a94435befaf1c64ea4f22e
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

Loading…