Isopropanol → HCID 178463187, compound

HRID 1014955Notes

Reaction equation

HRID 1014955 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([C:14]2[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=2)[O:7][C@H:6]1[N:21]1[CH:29]=[N:28][C:27]2[C:22]1=[N:23][C:24]([Cl:31])=[N:25][C:26]=2Cl)(=[O:3])[CH3:2].CC([N:36]([C@H:40]1[CH2:45][CH2:44][C@H:43]([NH2:46])[CH2:42][CH2:41]1)[C:37](=[O:39])[O-:38])(C)C.C(N(CC)[CH:51]([CH3:53])[CH3:52])(C)C.[CH:56](O)(C)C>>[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([C:14]2[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=2)[O:7][C@H:6]1[N:21]1[CH:29]=[N:28][C:27]2[C:22]1=[N:23][C:24]([Cl:31])=[N:25][C:26]=2[NH:46][C@H:43]1[CH2:42][CH2:41][C@H:40]([NH:36][C:37]([O:38][C:51]([CH3:53])([CH3:56])[CH3:52])=[O:39])[CH2:45][CH2:44]1)(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 81531DiisopropylethylamineHCID 12151756acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(2,6-dichloro-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)-tetrahydro-furan-3-yl esterHCID 178449843HCID 178449843, compound

Product 1

HCID 178463187HCID 178463187, compound

Conditions

Temperature
65 °C

Procedure

(2R,3R,4R,5R)-2-(2,6-Dichloro-9H-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-3,4-diyl diacetate (10 g) (ref WO98/28319A1) was suspended in isopropanol (100 ml). 1,1-Dimethylethyl(trans-4-aminocyclohexyl)carbamate (4.56 g) and N,N-diisopropylethylamine (5.6 ml) were added and the mixture heated at 65° C. under nitrogen overnight. The reaction mixture was allowed to cool to room temperature and evaporated down in vacuo. The residue was partitioned between ethyl acetate and water. The organic phase was separated and the aqueous extracted twice with ethyl acetate. The organic phases were combined, washed with water, dried (Na2SO4), and evaporated down in vacuo, dried under high vacuum overnight, to give the title compound, 12.49 g.

Workup

  1. temperatureto cool to room temperature
  2. customevaporated down in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe organic phase was separated
  5. extractionthe aqueous extracted twice with ethyl acetate
  6. washwashed with water
  7. dry with materialdried (Na2SO4)
  8. customevaporated down in vacuo
  9. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-3e7be318e233436ab22fb7a15546084d
Source dataset
uspto-grants-2011_07
Patent number
US07985740B2

Reaction notes

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