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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 1656797
ノート
印刷プレビュー

反応式

HRID 1656797 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 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

生成物 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 acid収率 85.2%

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

実験手順

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).

後処理

  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.

出典と根拠

ORDレコード
ord-b3b6ff60680543e484f563e8726def1d
出典データセット
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05254716

反応ノート

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