Hydrochloric Acid → HCID 69557573, compound

HRID 1934432Notes

Reaction equation

HRID 1934432 reaction equation
C[O:2][C:3](=[O:35])[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]=[CH:25][C:24]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=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:35])=[O:2])=[N:11][CH:10]=[N:9][C:8]=2[N:12]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:13]=1[CH2:20][CH3:21])=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69558941HCID 69558941, compound

Product 1

HCID 69557573HCID 69557573, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 150 mg (0.317 mmol) of [[5-(aminooxoacetyl)-6-ethyl-7-([1,1′-biphenyl] -2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester and 10 mL of methanol were treated with 0.95 mL of 2 M sodium hydroxide and heated to reflux for 4 hours. The reaction was cooled to ambient temperature then adjusted to pH 2 by the addition of 1 M HCl. The mixture was concentrated to a minimum volume and the residual liquid decanted from the solids. The solids were dried in vacuo to provide 92 mg (63%) of [[5-(aminooxoacetyl)-6-ethyl-7-([1,1′-biphenyl]-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid as a tan foam. nmr (300 MHz, dmso-d6) δ1.15 (t, J=7.4 Hz, 3H), 2.64 (q, J=7.4 Hz, 2H), 4.90 (s, 2H), 5.46 (s, 2H), 6.60 (d, J=7.2 Hz, 1H), 7.2-7.6 (m, 9H), 7.99 (s, 1H), 8.43 (s, 1H)

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. concentrationThe mixture was concentrated to a minimum volume
  4. customthe residual liquid decanted from the solids
  5. customThe solids were dried in vacuo

Sources & evidence

ORD record
ord-660b449a37ea46e7beec259906d5855d
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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