Sodium Hydroxide → 5-Deazaaminopterin

HRID 1388499

반응식

HRID 1388499 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 972725-Deazaaminopterin

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A solution of the product obtained in Example 2, VII (R1 =C2H5) (359 mg, 0.724 mmol) in dimethyl sulfoxide (10 ml) under N2 was treated with 1 N 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 1 N 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 (ε×10-3): 0.1 N HCl --218 (40.5), 280 sh (16.9), 300 (18.8); pH 7--218 (38.5), 2.45 (19.2), 280 (23.9), 296 sh (22.7); 0.1 N 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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1b7abc98154c446481e1b260390a3fc5
출처 데이터셋
uspto-grants-1984_02
특허 번호
US04431805

연결된 노트

불러오는 중…