Hydrochloric Acid → [[2-methoxy-5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid

HRID 1934430Notes

Reaction equation

HRID 1934430 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]([O:12][CH3:13])[N:11]=1.CO.[OH-].[Na+].Cl>O>[CH3:13][O: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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 69557788[[2-methoxy-5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester

Product 1

HCID 69557460[[2-methoxy-5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acidYield 56.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 40 mg of [[2-methoxy-5-(aminooxoacetyl)-6-ethyl-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester, 2.0 mL of methanol and 0.5 mL of 2 M sodium hydroxide were stirred at ambient temperature for 18 hours. The reaction was diluted with 10 mL of water and then adjusted to pH 4 with 1 M HCl providing a precipitate. The precipitate was collected by filtration and washed with 5 mL of water and dried in vacuo (40° C., 10 torr) to provide 22 mg of [[2-methoxy-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) δ0.98 (t, J=7.5 Hz, 3H), 2.89 (q, J=7.5 Hz, 2H), 3.87 (s, 3H), 4.87 (s, 2H), 5.48 (s, 2H), 7.17 (d, J=7.3 Hz, 2H), 7.31 (m, 3H), 7.50 (s, 1H), 7.93 (s, 1H), 12.89 (bs, 1H)

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with 5 mL of water
  3. customdried in vacuo (40° C., 10 torr)

Sources & evidence

ORD record
ord-e47aefb592dc4b3386473f9f9f405d53
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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