Hydrochloric Acid → N-[4-[2-(2-amino-4,5,6,7-tetrahydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid

HRID 1656797Notes

Reaction equation

HRID 1656797 reaction equation
C([O:3][C:4](=[O:35])[C@H:5]([CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])[NH:6][C:7](=[O:27])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH:16]2[C:24]3[C:23](=[O:25])[NH:22][C:21]([NH2:26])=[N:20][C:19]=3[NH:18][CH2:17]2)=[CH:10][CH:9]=1)C.Cl>[OH-].[Na+]>[NH2:26][C:21]1[NH:22][C:23](=[O:25])[C:24]2[CH:16]([CH2:15][CH2:14][C:11]3[CH:12]=[CH:13][C:8]([C:7]([NH:6][C@H:5]([C:4]([OH:35])=[O:3])[CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[O:27])=[CH:9][CH:10]=3)[CH2:17][NH:18][C:19]=2[N:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 136062642N-[4-[2-(2-amino-4,5,6,7-tetrahydro-4-oxo 3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid diethyl ester

Product 1

HCID 135515549N-[4-[2-(2-amino-4,5,6,7-tetrahydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acidYield 85.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1.50 grams (3.09 mmol) of N-[4-[2-(2-amino-4,5,6,7-tetrahydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid diethyl ester in 25 ml 1N NaOH was stirred at room temperature for 3 hours. The solution was carefully acidified to a of pH 2.8 by addition of 6 M aqueous HCl and the resulting suspension was then filtered. The precipitate was consecutively washed with 20 ml water, 10 ml methanol, 10 ml ether, and dried overnight at 50° C. and 10 torr. 1.13 g (85% of theory) of N-[4-[2-(2-amino-4,5,6,7-tetrahydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid was obtained as an amorphous solid. Selected data: 1H NMR (DMSO-d6) δ 12.20 (bs, 2H), 9.83 (bs, 1H), 8.48 (d, J=7.7 Hz, 1H), 7.74 (d, J=8.1 Hz, 2H), 7.26 (d, J=8.1 Hz, 2H), 6.32 (bs, 2H), 6.28 (bs, 1H), 4.33 (m, 1H), 3.43 (m, 1H), 3.01 (m, 2H), 2.61 (t, J=8.0 Hz, 2H), 2.30 (t, J=7.4 Hz, 2H), 1.96 (m, 3H), 1.54 (m, 1H); 13C NMR (DMSO-d6) 173.7, 173.1, 169.4, 166.5, 159.0, 156.7, 146.2, 131.4, 127.9, 127.2, 89.1, 52.1, 49.3, 36.9, 35.5, 32.3, 30.5, 26.2; IR (KBr) 3366, 2931, 1639, 1503, 1451, 1091 cm-1 ; MS(FAB) m/z 430 (MH+); UV (EtOH) 220 nm (ε 27 660), 280 (11 300).

Workup

  1. filtrationthe resulting suspension was then filtered
  2. washThe precipitate was consecutively washed with 20 ml water, 10 ml methanol, 10 ml ether
  3. customdried overnight at 50° C.

Sources & evidence

ORD record
ord-b3b6ff60680543e484f563e8726def1d
Source dataset
uspto-grants-1993_10
Patent number
US05254716

Reaction notes

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