Phenyl isocyanate → 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-N6-benzoyl-3'-O-phenylcarbamoyladenosine

HRID 889777

반응식

HRID 889777 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:65]2[CH:70]=[CH:69][C:68]([O:71][CH3:72])=[CH:67][CH:66]=2)([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[O:32][CH2:33][C@H:34]2[O:38][C@@H:37]([N:39]3[C:56]4[N:55]=[CH:54][N:53]=[C:43]([NH:44][C:45](=[O:52])[C:46]5[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=5)[C:42]=4[N:41]=[CH:40]3)[C@H:36]([OH:57])[C@@H:35]2[OH:58])=[CH:27][CH:26]=1.[C:73]1([N:79]=[C:80]=[O:81])[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=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=CN=C(NC(=O)C5C=CC=CC=5)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>[CH3:72][O:71][C:68]1[CH:67]=[CH:66][C:65]([C:31]([C:28]2[CH:27]=[CH:26][C:25]([O:24][CH3:23])=[CH:30][CH:29]=2)([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[O:32][CH2:33][C@H:34]2[O:38][C@@H:37]([N:39]3[C:56]4[N:55]=[CH:54][N:53]=[C:43]([NH:44][C:45](=[O:52])[C:46]5[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=5)[C:42]=4[N:41]=[CH:40]3)[C@H:36]([OH:57])[C@@H:35]2[O:58][C:80](=[O:81])[NH:79][C:73]2[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=2)=[CH:70][CH:69]=1

참가 물질

8

반응물 5

HCID 7672Phenyl isocyanateHCID 11430Potassium CarbonateHCID 688211(S,S)-2,6-Bis(4-isopropyl-2-oxazolin-2-yl)pyridineHCID 142821355'-DMT-Bz-rAHCID 668426065'-O-[bis(4-methoxyphenyl)phenylmethyl]-N6-benzoyl-2'-O-phenylcarbamoyladenosine

생성물 1

HCID 668427225'-O-[bis(4-methoxyphenyl)phenylmethyl]-N6-benzoyl-3'-O-phenylcarbamoyladenosine

시약·촉매·용매 2

HCID 2734996copper(II) trifluoromethanesulfonate촉매HCID 8028Tetrahydrofuran용매3회

실험 절차

The THF solution (75 ml) containing 2,6-bis[(4S)-isopropyl-2-oxazoline-2-yl]pyridine (0.15 mmol, 45.2 mg) and copper chloride (II) (0.15 mmol, 25.6 mg) was stirred for a day at room temperature. After the reaction mixture was cooled to −15° C., the THF solution (15 ml) of 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-N6-benzoyladenosine (1.5 mmol, 1.0 g) and the THF solution (15 ml) of phenyl isocyanate (1.5 mmol, 178.7 mg) and K2CO3 (1.5 mmol, 207.3 mg) were added thereto. After the mixture was continuously stirred for 42 hours at −15° C., the mixture was analyzed with high-performance liquid chromatography. As a result, it was found that 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-N6-benzoyl-2′-O-phenylcarbamoyladenosine and 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-N6-benzoyl-3′-O-phenylcarbamoyladenosine were produced at the ratio of 93:7, and the transformation ratio of the reaction was 99%.

후처리

  1. temperatureAfter the reaction mixture was cooled to −15° C.
  2. stirringAfter the mixture was continuously stirred for 42 hours at −15° C.

출처 및 근거

ORD 기록
ord-ae90ea5387c9477da37e95858a7ff07b
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252919B2

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