Ethanol → (3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-[(4-pyridin-2-yltriazol-1-yl)methyl]-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol

HRID 335489노트

반응식

HRID 335489 반응식
[N:1]([CH2:4][C@H:5]1[O:13][C@H:12]2[C@H:8]([N:9]=[C:10]([NH:14][CH2:15][CH3:16])[S:11]2)[C@@H:7]([OH:17])[C@@H:6]1[OH:18])=[N+:2]=[N-:3].C(O)C.[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)#[CH:23]>[Cu].O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].O.CC(O)(C)C>[CH2:15]([NH:14][C:10]1[S:11][C@H:12]2[O:13][C@H:5]([CH2:4][N:1]3[CH:23]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[N:3]=[N:2]3)[C@@H:6]([OH:18])[C@H:7]([OH:17])[C@H:8]2[N:9]=1)[CH3:16]

참가 물질

8

반응물 3

HCID 702EthanolHCID 137268EthynylpyridineHCID 66550531CID 66550531

생성물 1

HCID 178463442(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-[(4-pyridin-2-yltriazol-1-yl)methyl]-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol수율 25.5%

시약·촉매·용매 4

HCID 23978Copper촉매HCID 24463Copper sulfate pentahydrate촉매HCID 962Water용매2회HCID 6386tert-Butanol용매

실험 절차

In a 5 mL seal vial equipped with a stir bar, a septum was added (3aR,5R,6S,7R,7aR)-5-(azidomethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol (40.00 mg; 0.15 mmol; 1.00 eq.), copper Not supported by ACD (65.10 mg; 1.02 mmol; 7.00 eq.) and copper (2+) sulfate pentahydrate (7.31 mg; 0.03 mmol; 0.20 eq.). The vial was evacuated and filled with N2. This procedure was repeated for twice before ethanol (0.40 ml)/water (0.60 ml)/2-methylpropan-2-ol (1.00 ml) and 2-ethynylpyridine (0.03 ml; 0.29 mmol; 2.00 eq.) was added into the mixture. The mixture was stirred at room temperature for overnight before 3 mL H2O was added into the mixture and dried via lyophilization. The mixture was purified with Yamazen C1 acidic condition affording 14.4 mg (20.1%) of the title compound as a white solid (HPLC 99%, retention time=1.73 min) once lyophilized.

후처리

  1. customIn a 5 mL seal vial
  2. customequipped with a stir bar
  3. customThe vial was evacuated
  4. additionfilled with N2
  5. additionwas added into the mixture
  6. additionwas added into the mixture
  7. customdried via lyophilization
  8. customThe mixture was purified with Yamazen C1 acidic condition

출처 및 근거

ORD 기록
ord-74622ff6de5c450cb416fb212d82cd9b
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08884023B2

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