Phenyl isocyanate → 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-O-phenylcarbamoyl-uridine

HRID 889768

반응식

HRID 889768 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:55]2[CH:60]=[CH:59][C:58]([O:61][CH3:62])=[CH:57][CH:56]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[O:32][CH2:33][C@H:34]2[O:38][C@@H:37]([N:39]3[CH:46]=[CH:45][C:43](=[O:44])[NH:42][C:40]3=[O:41])[C@H:36]([OH:47])[C@@H:35]2[OH:48])=[CH:27][CH:26]=1.[C:63]1([N:69]=[C:70]=[O:71])[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1.COC1C=CC(C(C2C=CC(OC)=CC=2)(C2C=CC=CC=2)OC[C@H]2O[C@@H](N3C=CC(=O)NC3=O)[C@H](OC(=O)NC3C=CC=CC=3)[C@@H]2O)=CC=1>[Cu](Cl)Cl.C1COCC1>[CH3:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([C:31]([C:55]2[CH:56]=[CH:57][C:58]([O:61][CH3:62])=[CH:59][CH:60]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[O:32][CH2:33][C@H:34]2[O:38][C@@H:37]([N:39]3[CH:46]=[CH:45][C:43](=[O:44])[NH:42][C:40]3=[O:41])[C@H:36]([OH:47])[C@@H:35]2[O:48][C:70](=[O:71])[NH:69][C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)=[CH:29][CH:30]=1

참가 물질

7

반응물 4

HCID 7672Phenyl isocyanateHCID 688211(S,S)-2,6-Bis(4-isopropyl-2-oxazolin-2-yl)pyridineHCID 117633095'-O-(Bis(4-methoxyphenyl)phenylmethyl)uridineHCID 442506525'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-phenylcarbamoyl-uridine

생성물 1

HCID 668425975'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-O-phenylcarbamoyl-uridine

시약·촉매·용매 2

HCID 24014Cupric Chloride촉매HCID 8028Tetrahydrofuran용매3회

실험 절차

The THF solution (1.5 ml) containing 2,6-bis[(4S)-isopropyl-2-oxazoline-2-yl]pyridine (0.03 mmol, 9.1 mg) and copper chloride (II) (0.03 mmol, 4.1 mg) was stirred for one day at room temperature. After the reaction mixture was cooled to −30° C., the THF solution (1.5 ml) of 5′-O-[bis(4-methoxyphenyl)phenylmethyl]uridine (0.3 mmol, 164.3 mg) and the THF solution (1.5 ml) of phenyl isocyanate (0.3 mmol, 35.8 mg) were added thereto. After the mixture was continuously stirred for two hours at −30° C., the mixture was analyzed with high-performance liquid chromatography. As a result, it was found that 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-2′-O-phenylcarbamoyl-uridine and 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-3′-O-phenylcarbamoyl-uridine were produced at the ratio of 97:3, and the transformation ratio of the reaction was not less than 99%.

후처리

  1. temperatureAfter the reaction mixture was cooled to −30° C.
  2. stirringAfter the mixture was continuously stirred for two hours at −30° C.

출처 및 근거

ORD 기록
ord-6dfbc551e4694c47b6606f71616a6091
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252919B2

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