Hydrochloric Acid → HCID 69557550, compound

HRID 1934437Notes

Reaction equation

HRID 1934437 reaction equation
C[O:2][C:3](=[O:30])[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]([F:29])[CH:24]=3)[C:8]=2[N:9]=[CH:10][N:11]=1.[OH-].[Na+].Cl>CO>[NH2:18][C:16](=[O:17])[C:15]([C:14]1[C:7]2[C:6]([O:5][CH2:4][C:3]([OH:30])=[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]([F:29])[CH:24]=2)[C:13]=1[CH2:20][CH3:21])=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69558262HCID 69558262, compound

Product 1

HCID 69557550HCID 69557550, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 28 mg (0.067 mmol) of [[5-(aminooxoacetyl)-6-ethyl-7-[(3-fluorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester and 5 mL of methanol were treated with 0.05 mL of 2 M sodium hydroxide and stirred at ambient temperature for 22 hours. The reaction was adjusted to pH 3 by the addition of 1 M HCl and concentrated to provide 10 mg (40%) of [[5-(aminooxoacetyl)-6-ethyl-7-[(3-fluorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid as a white solid. nmr (300 MHz, dmso-d6) δ1.02 (t, 3H), 2.94 (q, 2H), 4.91 (s, 2H), 5.59 (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), 8.45 (s, 1H)

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-4fbaa6b72b274f6da452997dd97f90a4
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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