Sodium Hydroxide → 5-Deazaaminopterin

HRID 1248977

反応式

HRID 1248977 の反応式
[NH2:1][C:2]1[N:3]=[C:4]([NH2:36])[C:5]2[CH:11]=[C:10]([CH2:12][NH:13][C:14]3[CH:35]=[CH:34][C:17]([C:18]([NH:20][C@H:21]([C:29]([O:31]CC)=[O:30])[CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])=[O:19])=[CH:16][CH:15]=3)[CH:9]=[N:8][C:6]=2[N:7]=1.[OH-].[Na+]>CS(C)=O>[NH2:1][C:2]1[N:3]=[C:4]([NH2:36])[C:5]2[CH:11]=[C:10]([CH2:12][NH:13][C:14]3[CH:35]=[CH:34][C:17]([C:18]([NH:20][C@H:21]([C:29]([OH:31])=[O:30])[CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[O:19])=[CH:16][CH:15]=3)[CH:9]=[N:8][C:6]=2[N:7]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 12908481Diethyl N-[4-[(2,4-diaminopyrido[2,3-d]pyrimidin-6-yl)methylamino]benzoyl]-L-glutamate

生成物 1

HCID 972725-Deazaaminopterin

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A solution of the product obtained in Example 3, VII (R=H, R1 =C2H5) (359 mg, 0.724 mmol) in dimethyl sulfoxide (10 ml) under N2 was treated with 1N NaOH (1.81 ml, 1.81 mmol), stirred in a stoppered flask under N2 for 6 hours, and evaporated to dryness in vacuo at <30° C. A solution of the residue in water (18 ml) was filtered and acidified to pH 3.6 with 1N HCl. The precipitate was collected by filtration, washed with water at pH 3.6 and dried in vacuo (P2O5); yield 297 mg (87%), mp indefinite (softens above 200° C.); mass spectrum, m/e 440 (M+1)+ ; λmax nm (εx 10-3): 0.1N HCl-218 (40.5), 280 sh (16.9), 300 (18.8); pH 7-218 (38.5), 245 (19.2), 280 (23.9), 296 sh (22.7); 0.1N NaOH-248 (22.0), 280 (24.4), 296 sh (22.7), 345 (7.75); 1H-NMR (DMSO-d6, 6% w/v), δ2.00 m (CH2CH2CO), 2.29 t (CH2CO), 4.36 m (CHN, CH2N), 6.66 d, 7.68 d (C6H4), 7.41 (NH2), 8.04 m (NH2, NH, CO2H), 8.52 d, 8.70 d (5-CH, 7-CH).

後処理

  1. customevaporated to dryness in vacuo at <30° C
  2. filtrationA solution of the residue in water (18 ml) was filtered
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water at pH 3.6
  5. dry with materialdried in vacuo (P2O5)
  6. customyield 297 mg (87%), mp indefinite (softens above 200° C.)
  7. wait1H-NMR (DMSO-d6, 6% w/v), δ2.00 m (CH2CH2CO), 2.29 t (CH2CO), 4.36 m (CHN, CH2N), 6.66 d, 7.68 d
  8. custom(C6H4), 7.41 (NH2), 8.04 m (NH2, NH, CO2H), 8.52 d, 8.70 d (5-CH, 7-CH)

出典と根拠

ORDレコード
ord-0b31ee00bdec4d9594ae93d7aad6cc2f
出典データセット
uspto-grants-1986_12
特許番号
US04628089

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