Sodium Hydroxide → HCID 9932328, compound

HRID 1934426Notes

Reaction equation

HRID 1934426 reaction equation
C[O:2][C:3](=[O:31])[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][CH:26]=3)[C:8]=2[N:9]=[C:10]([S:12][CH3:13])[N:11]=1.[OH-].[Na+]>C(O)C>[CH3:13][S:12][C:10]1[N:11]=[C:6]([O:5][CH2:4][C:3]([OH:31])=[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][CH:26]=3)[C:8]=2[N:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69558786HCID 69558786, compound

Product 1

HCID 9932328HCID 9932328, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

A suspension of 99.5 mg (0.225 mmol) of [[2-(methylthio)-5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester in 8.0 mL of ethanol was treated with 0.175 mL of 2 M sodium hydroxide and the mixture heated to 65° C. for 1 hour. The reaction mixture was cooled to ambient temperature and concentrated under vacuum to a white solid. The solid was dissolved in 12 mL of water and the product precipitated upon the addition of 0.40 mL of 1 M HCl. The solids were collected by filtration, washed with 10 mL of water, then dried in vacuo (40° C., 10 torr) to provide 78 mg (81%) of [[2-(methylthio)-5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-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), 2.49 (s, 3H), 2.91 (q, J=7.4 Hz, 2H), 4.89 (s, 2H), 5.52 (s, 2H), 7.15 (d, J=7.2 Hz, 2H), 7.32 (m, 3H), 7.55 (s, 1H), 7.97 (s, 1H), 13.02 (bs, 1H)

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. concentrationconcentrated under vacuum to a white solid
  3. dissolutionThe solid was dissolved in 12 mL of water
  4. customthe product precipitated upon the addition of 0.40 mL of 1 M HCl
  5. filtrationThe solids were collected by filtration
  6. washwashed with 10 mL of water
  7. customdried in vacuo (40° C., 10 torr)

Sources & evidence

ORD record
ord-d7f51410643d4d02a8eb2b6a2adf906f
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

Loading…