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 335489ノート

反応式

HRID 335489 の反応式
[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]

参加物

8

反応物 3

HCID 702EthanolHCID 137268EthynylpyridineHCID 66550531CID 66550531

生成物 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-diol収率 25.5%

試薬・触媒・溶媒 4

HCID 23978Copper触媒HCID 24463Copper sulfate pentahydrate触媒HCID 962Water溶媒2 回HCID 6386tert-Butanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-74622ff6de5c450cb416fb212d82cd9b
出典データセット
uspto-grants-2014_11
特許番号
US08884023B2

反応ノート

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