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

HRID 889777ノート

反応式

HRID 889777 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 2734996copper(II) trifluoromethanesulfonate触媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

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%.

後処理

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

出典と根拠

ORDレコード
ord-ae90ea5387c9477da37e95858a7ff07b
出典データセット
uspto-grants-2012_08
特許番号
US08252919B2

反応ノート

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