Sodium Hydroxide → HCID 69557983, compound

HRID 1934442Notes

Reaction equation

HRID 1934442 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]([F:31])[CH:26]=3)[C:8]=2[N:9]=[C:10]([S:12][CH3:13])[N:11]=1.[OH-].[Na+]>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]([F:31])[CH:26]=3)[C:8]=2[N:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69558654HCID 69558654, compound

Product 1

HCID 69557983HCID 69557983, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 260 mg (0.564 mmol) of [[2-(methylthio)-5-(aminooxoacetyl)-6-ethyl-7-[(3-fluorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester and 25 mL of methanol were treated with 0.42 mL of 2 M sodium hydroxide and stirred at reflux for 3 hours. The reaction was cooled to ambient temperature. The product precipitated upon addition of 1 M HCl and was collected by filtration. The solids were washed with water and dried in vacuo to provide 176 mg (73%) of [[2-(methylthio)-5-(aminooxoacetyl)-6-ethyl-7-[(3-fluorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid as a solid. nmr (300 MHz, dmso-d6) δ0.99 (t, 3H), 2.49 (s, 3H), 2.91 (q, 2H), 4.87 (s, 2H), 5.52 (s, 2H), 6.90 (d, 1H), 7.04 (d, 1H), 7.10 (dt, 1H), 7.36 (dt, 1H), 7.60 (br s, 1H), 8.02 (br s, 1H)

Workup

  1. temperatureat reflux for 3 hours
  2. customThe product precipitated upon addition of 1 M HCl
  3. filtrationwas collected by filtration
  4. washThe solids were washed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ea26baba884d4948b397aa4ddb00bcf9
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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