Methanol → 2-Amino-9-(4-butyryloxy-3-hydroxymethylbut-1-yl)purine

HRID 5870

반응식

HRID 5870 반응식
OCC(C(OC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)OC)CC[N:6]1[C:14]([NH:15]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:13][C:12]2C1=NC(OC)=[N:10][CH:11]=2.[C:60]([O:65][C:66](=O)[CH2:67][CH2:68][CH3:69])(=[O:64])[CH2:61][CH2:62][CH3:63].[CH3:71][OH:72].C[N:74]([CH3:77])[CH:75]=O>CN(C)C1C=CN=CC=1>[NH2:15][C:14]1[N:6]=[C:77]2[C:11]([N:10]=[CH:75][N:74]2[CH2:69][CH2:68][CH:67]([CH2:71][OH:72])[CH2:66][O:65][C:60](=[O:64])[CH2:61][CH2:62][CH3:63])=[CH:12][N:13]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 6228DimethylformamideHCID 7798Butyric anhydrideHCID 678620909-(3-Hydroxymethyl-4-monomethoxytrityloxybut-1-yl)-2-monomethoxytritylaminopurine

생성물 1

HCID 138831932-Amino-9-(4-butyryloxy-3-hydroxymethylbut-1-yl)purine

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine촉매

실험 절차

To a solution of 9-(3-hydroxymethyl-4-monomethoxytrityloxybut-1-yl)-2-monomethoxytritylaminopurine (0.70 g, 0.9 mmol) and 4-dimethylaminopyridine (10 mg) in N,N-dimethylformamide (5 ml) was added butyric anhydride (0.29 ml, 1.8 mmol) and the solution was stirred for 15 minutes. Methanol (1 ml) was added and the solvent was removed. The residue was taken up in 80% acetic acid (9 ml) and the solution was stirred at 70° for 30 minutes. Water (2 ml) was added and the solution was extracted with hexane (2×10 ml). The aqueous layer was retained and the solvent was removed. The residue was partitioned between saturated aqueous sodium bicarbonate and chloroform and the organic layer was dried (magnesium sulphate) and the solvent removed. The residue was purified by column chromatography on silica gel eluting with chloroform-methanol (16:1 to afford 2-amino-9-(4-butyryloxy-3-hydroxymethylbut-1-yl)purine which was obtained as a white crystalline solid after trituration with methanol (188 mg, 68%), m.p. 125°-127°; λmax (MeOH) 222 (27,600), 243 (4,830), and 308 (6,950)nm; νmax (KBr) 3190, 1730, 1640, 1620, and 1580 cm-1 ; δH [(CD3)2SO]0.85 (3H, t, J 7.4 Hz, CH3), 1.50 (2H, sextet, J 7.3 Hz, CH2CH2CH3), 1.68 (1H, m, 3'-H), 1.82 (2H, m, 2'-H), 2.23 (2H, t, J 7.4 Hz, CH2CH2CH3), 3.42 (2H, t, J 5.2 Hz, D2O exchange gives d, CH2OH), 3.95-4.1 (2H, ABX, JAB 11.0 Hz, JAX =JBX 5.8 Hz, CH2OOC), 4.12 (2H, t, J 7.3 Hz, 1'-H), 4.62 (1H, t, J 4.9 Hz, D2O exchangeable, OH), 6.44 (2H, s, D2O exchangeable, 2-NH2), 8.06 (1H, s, 8-H), and 8.56 (1H, s, 6-H); (Found: C, 54.41; H, 6.91; N, 22.70%. C14H21N5O3 requires C, 54.71; H, 6.89; N, 22.79%).

후처리

  1. customthe solvent was removed
  2. stirringthe solution was stirred at 70° for 30 minutes
  3. additionWater (2 ml) was added
  4. extractionthe solution was extracted with hexane (2×10 ml)
  5. customthe solvent was removed
  6. customThe residue was partitioned between saturated aqueous sodium bicarbonate and chloroform
  7. dry with materialthe organic layer was dried (magnesium sulphate)
  8. customthe solvent removed
  9. customThe residue was purified by column chromatography on silica gel eluting with chloroform-methanol (16:1

출처 및 근거

ORD 기록
ord-4d1fd178952846efa63a1421db1f7aea
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246937

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