Hydrochloric Acid → [(1R,4S)-4-(6-aminopurin-9-yl)cyclopent-2-en-1-yl]methanol

HRID 986925ノート

反応式

HRID 986925 の反応式
[NH2:1]C1C(N[C@H]2C[C@@H](CO)C=C2)=NC=NC=1Cl.Cl[C:18]1[N:26]=[CH:25][N:24]=[C:23]2[C:19]=1[N:20]=[CH:21][N:22]2[C@H:27]1[CH2:31][C@@H:30]([CH2:32][OH:33])[CH:29]=[CH:28]1.Cl>C(OC(OCC)OCC)C>[NH2:1][C:18]1[N:26]=[CH:25][N:24]=[C:23]2[C:19]=1[N:20]=[CH:21][N:22]2[C@H:27]1[CH2:31][C@@H:30]([CH2:32][OH:33])[CH:29]=[CH:28]1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 86759192(1R,4S)-4-(6-Chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (1R,4S)-4-[(5-Amino-6-chloro-4-pyrimidinyl)amino]-2-cyclopentene-1-methanol

生成物 1

HCID 466400[(1R,4S)-4-(6-aminopurin-9-yl)cyclopent-2-en-1-yl]methanol

試薬・触媒・溶媒 1

HCID 31214Ethyl orthoformate溶媒

実験手順

(1R,4S)-4-(6-Chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (1R,4S)-4-[(5-Amino-6-chloro-4-pyrimidinyl)amino]-2-cyclopentene-1-methanol (from part d of this example, 9.63 g, 40.0 mmol), triethylorthoformate (150 mL), and concentrated hydrochloric acid (14 mL) were stirred for 3 hours. Volatiles were evaporated and the residual solid was partitioned between chloroform (300 mL) and saturated aqueous sodium carbonate (100 mL). The aqueous layer was extracted with chloroform (2×100 mL). The combined chloroform layers were dried (sodium sulfate). Volatiles were evaporated under reduced pressure and the residual yellow glass was chromatographed on silica gel. Elution with ethyl acetate gave title compound as white needles from ethyl acetate (7.45 g, 74%), m.p. 121-124° C.; 1H-NMR (DMSO-d6) δ: 8.81 (s, 1H), 8.64 (s, 1H), 6.24 and 6.21 (two m, 2H), 5.75 (m, 1H), 4.75 (t, J=5.4 Hz, 1H), 3.34 (m, 2H), 2.95 (m, 1H), 2.75 (m, 1H), 1.75 (m, 1H).

後処理

  1. customwere stirred for 3 hours
  2. customVolatiles were evaporated
  3. customthe residual solid was partitioned between chloroform (300 mL) and saturated aqueous sodium carbonate (100 mL)
  4. extractionThe aqueous layer was extracted with chloroform (2×100 mL)
  5. dry with materialThe combined chloroform layers were dried (sodium sulfate)
  6. customVolatiles were evaporated under reduced pressure
  7. customthe residual yellow glass was chromatographed on silica gel
  8. washElution with ethyl acetate

出典と根拠

ORDレコード
ord-ca0495f387ac4acd87b54475bfd030a1
出典データセット
uspto-grants-2003_10
特許番号
US06630477B1

反応ノート

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