p-(Chlorodiphenylmethyl)anisole → N4,5'-O-dibenzoyl-2'-fluoro-3'-(4-methoxytrityl)amino-2',3'-dideoxycytidine

HRID 342921노트

반응식

HRID 342921 반응식
[C:1]([NH:9][C:10]1[CH:32]=[CH:31][N:13]([C@@H:14]2[O:28][C@H:17]([CH2:18][O:19][C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@@H:16]([NH2:29])[C@H:15]2[F:30])[C:12](=[O:33])[N:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:34][O:35][C:36]1[CH:55]=[CH:54][C:39]([C:40](Cl)([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:38][CH:37]=1>N1C=CC=CC=1>[C:1]([NH:9][C:10]1[CH:32]=[CH:31][N:13]([C@@H:14]2[O:28][C@H:17]([CH2:18][O:19][C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@@H:16]([NH:29][C:40]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:39]3[CH:38]=[CH:37][C:36]([O:35][CH3:34])=[CH:55][CH:54]=3)[C@H:15]2[F:30])[C:12](=[O:33])[N:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 84462p-(Chlorodiphenylmethyl)anisoleHCID 54409373N4,5'-O-dibenzoyl-2'-fluoro-3'-amino-2',3'-dideoxycytidine

생성물 1

HCID 54559474N4,5'-O-dibenzoyl-2'-fluoro-3'-(4-methoxytrityl)amino-2',3'-dideoxycytidine

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

N4,5'-O-dibenzoyl-2'-fluoro-3'-(4-methoxytrityl)amino-2',3'-dideoxycytidine 14 was prepared as follows: To 0.9 g (2.0 mmol) of 13 in 25 mL anhydrous pyridine was added 0.86 g (2.8 mmol) 4-methoxytrityl chloride, and the mixture stirred overnight. The reaction was quenched with 0.5 mL H2O and concentrated in vacuo. CH2Cl2 (50 mL) was added and washed with 50 mL saturated aqueous NaHCO3 and with water (2×50 mL). The solvent was removed in vacuo, replaced with 10 mL CH2Cl2, and pipetted into 80 mL rapidly stirred 1/1 hexane/ether. After further stirring for 2 h, the product was collected by filtration and dried under vacuum, giving 1.3 g (88% yield) of product as a white powder. Mass-spectrometry, FAB+, M+H+, calculated: 725.2775, observed: 725.2761. 1H NMR δ 8.59 (br s, 1H), 8.07 (br d, J=5.7 Hz, 1H), 7.89 (br d, J=7 Hz, 2H), 7.83 (dd, J=1.3, 6.7 Hz, 2H), 7.68 (dd, J=7.4, 7.4 Hz, 2H), 7.5-7.6 (m, 8H), 7.43 (dd, J=2.1, 6.9 Hz, 2H), 7.1-7.3 (mm, 7H), 6.71 (d, J=8.9 Hz, 2H), 5.80 (d, J=15.4 Hz, 1H), 5.03 (dd, J=2.0, 13.0 Hz, 1H), 4.98 (dd, J=2.3;, 13.1 Hz, 1H),4.41 (brd,J=10.5 Hz, 1H),3.63 (s,3H),3.36(dddd,J=3.1, 11.1, 11.1, 25.7 Hz, 1H), 2.84 (dd, J=3.1, 49.9 Hz, 1H), 2.52 (dd, J=2.7, 11.5 Hz, 1H); 19F NMR δ -196.3 (m).

후처리

  1. customThe reaction was quenched with 0.5 mL H2O
  2. concentrationconcentrated in vacuo
  3. additionCH2Cl2 (50 mL) was added
  4. washwashed with 50 mL saturated aqueous NaHCO3 and with water (2×50 mL)
  5. customThe solvent was removed in vacuo
  6. stirringrapidly stirred 1/1 hexane/ether
  7. stirringAfter further stirring for 2 h
  8. filtrationthe product was collected by filtration
  9. customdried under vacuum

출처 및 근거

ORD 기록
ord-5cb618d15bf143c8a5f4e8343e3eb66b
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859233

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