Phenyl isocyanate → 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-N2-phenoxyacetyl-3'-O-phenylcarbamoylguanosine

HRID 889778

반응식

HRID 889778 반응식
C([C@H]1COC(C2C=CC=C(C3OC[C@H](C(C)C)N=3)N=2)=N1)(C)C.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([C:68]2[CH:73]=[CH:72][C:71]([O:74][CH3:75])=[CH:70][CH:69]=2)([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)[O:32][CH2:33][C@H:34]2[O:38][C@@H:37]([N:39]3[C:59]4[N:58]=[C:46]([NH:47][C:48](=[O:57])[CH2:49][O:50][C:51]5[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=5)[NH:45][C:43](=[O:44])[C:42]=4[N:41]=[CH:40]3)[C@H:36]([OH:60])[C@@H:35]2[OH:61])=[CH:27][CH:26]=1.[C:76]1([N:82]=[C:83]=[O:84])[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1.C([O-])([O-])=O.[K+].[K+].COC1C=CC(C(C2C=CC(OC)=CC=2)(C2C=CC=CC=2)OC[C@H]2O[C@@H](N3C4N=C(NC(=O)COC5C=CC=CC=5)NC(=O)C=4N=C3)[C@H](OC(=O)NC3C=CC=CC=3)[C@@H]2O)=CC=1>C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Cu+2].C1COCC1>[CH3:75][O:74][C:71]1[CH:70]=[CH:69][C:68]([C:31]([C:28]2[CH:27]=[CH:26][C:25]([O:24][CH3:23])=[CH:30][CH:29]=2)([C:62]2[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=2)[O:32][CH2:33][C@H:34]2[O:38][C@@H:37]([N:39]3[C:59]4[N:58]=[C:46]([NH:47][C:48](=[O:57])[CH2:49][O:50][C:51]5[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=5)[NH:45][C:43](=[O:44])[C:42]=4[N:41]=[CH:40]3)[C@H:36]([OH:60])[C@@H:35]2[O:61][C:83](=[O:84])[NH:82][C:76]2[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=2)=[CH:73][CH:72]=1

참가 물질

8

반응물 5

HCID 7672Phenyl isocyanate2회HCID 11430Potassium CarbonateHCID 688211(S,S)-2,6-Bis(4-isopropyl-2-oxazolin-2-yl)pyridineHCID 136368406N2-Phenoxyacetyl-5'-O-(4,4'-dimethoxytrityl)guanosineHCID 1363978965'-O-[bis(4-methoxyphenyl)phenylmethyl]-N2-phenoxyacetyl-2'-O-phenylcarbamoylguanosine

생성물 1

HCID 1363978905'-O-[bis(4-methoxyphenyl)phenylmethyl]-N2-phenoxyacetyl-3'-O-phenylcarbamoylguanosine

시약·촉매·용매 2

HCID 2734996copper(II) trifluoromethanesulfonate촉매HCID 8028Tetrahydrofuran용매4회

실험 절차

The THF solution (33 ml) containing 2,6-bis[(4S)-isopropyl-2-oxazoline-2-yl]pyridine (0.06 mmol, 18.1 mg) and copper chloride (II) (0.06 mmol, 10.2 mg) was stirred for a day at room temperature. After the reaction mixture was cooled to −20° C., the THF solution (32 ml) of 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-N2-phenoxyacetyl-guanosine (0.60 mmol, 431.8 mg) and the THF solution (1.6 ml) of phenyl isocyanate (0.60 mmol, 71.5 mg) and K2CO3 (0.60 mmol, 82.9 mg) were sequentially added thereto. After the mixture was stirred for 24.5 hours at −20° C., the THF solution (1.6 ml) of phenyl isocyanate (0.60 mmol, 71.5 mg) was added thereto. After the mixture was further stirred for 23.5 hours, the mixture was analyzed with high-performance liquid chromatography. As a result, it was found that 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-N2-phenoxyacetyl-2′-O-phenylcarbamoylguanosine and 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-N2-phenoxyacetyl-3′-O-phenylcarbamoylguanosine were produced at the ratio of 99:1, and the transformation ratio of the reaction was not less than 99%.

후처리

  1. temperatureAfter the reaction mixture was cooled to −20° C.
  2. stirringAfter the mixture was stirred for 24.5 hours at −20° C.
  3. stirringAfter the mixture was further stirred for 23.5 hours

출처 및 근거

ORD 기록
ord-cf14502cf9a843679917458ba481868b
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252919B2

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