Sodium Hydroxide → HCID 69557711, compound

HRID 1934456Notes

Reaction equation

HRID 1934456 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][O:5][C:6]1[C:7]2[C:14]([C:15](=[O:19])[C:16]([NH2:18])=[O:17])=[C:13]([CH2:20][CH3:21])[N:12]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[C:8]=2[N:9]=[CH:10][N:11]=1.[OH-].[Na+]>CO>[NH2:18][C:16](=[O:17])[C:15]([C:14]1[C:7]2[C:6]([O:5][CH2:4][C:3]([OH:33])=[O:2])=[N:11][CH:10]=[N:9][C:8]=2[N:12]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:32])[F:31])[CH:24]=2)[C:13]=1[CH2:20][CH3:21])=[O:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69558357HCID 69558357, compound

Product 1

HCID 69557711HCID 69557711, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 70 mg (0.15 mmol) of [[5-(aminooxoacetyl)-6-ethyl-7-[[3-(trifluoromethyl)phenyl]methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester and 2 mL of methanol were treated with 0.15 mL of 2 M sodium hydroxide and stirred at ambient temperature for 3 days. The reaction was concentrated to an oil then diluted with 5 mL of water. The product precipitated upon the addition of 0.45 mL of 1 M HCl to provide 60 mg (90%) of [[5-(aminooxoacetyl)-6-ethyl-7-[[3-(trifluoromethyl)phenyl]-methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid as a white solid. nmr (500 MHz, dmso-d6) δ1.00 (t, J=7.4 Hz, 3H), 2.98 (q, J=7.4 Hz, 2H), 4.92 (s, 2H), 5.70 (s, 2H), 7.31 (d, J=7.8 Hz, 1H), 7.53 (t, J=7.8 Hz, 1H) 7.58 (br s, 1H), 7.65 (m, 2H), 8.00 (br s, 1H), 8.46 (s, 1H)

Workup

  1. concentrationThe reaction was concentrated to an oil
  2. additionthen diluted with 5 mL of water
  3. customThe product precipitated upon the addition of 0.45 mL of 1 M HCl

Sources & evidence

ORD record
ord-a81f42ba4e494280a8dcda685bf88d13
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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