Isopropanol → HCID 178463187, compound

HRID 1014954Notes

Reaction equation

HRID 1014954 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].C(N(CC)[CH:36]([CH3:38])[CH3:37])(C)C.CC([N:45]([C@H:49]1[CH2:54][CH2:53][C@H:52]([NH2:55])[CH2:51][CH2:50]1)[C:46](=[O:48])[O-:47])(C)C.[CH3:56]C(O)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:55][C@H:52]1[CH2:51][CH2:50][C@H:49]([NH:45][C:46]([O:47][C:36]([CH3:38])([CH3:56])[CH3:37])=[O:48])[CH2:54][CH2:53]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

To stirred (2R,3R,4R,5R)-2-(2,6-dichloro-9H-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-3,4-diyl diacetate (ref WO98/28319A1) (15 g) in propan-2-ol (100 ml) was added N,N-diisopropylethylamine (7.7 ml) and 1,1-dimethylethyl(trans-4-aminocyclohexyl)carbamate (6.82 g). The mixture was stirred at 65° C. for 24 h before cooling to room temperature and concentrating in vacuo. The crude product was purified by column chromatography (silica) eluting with 30% cyclohexane in ethyl acetate. The appropriate fractions were combined and concentrated in vacuo and triturated with diethyl ether to yield the title compound as a white solid, 8.56 g.

Workup

  1. temperaturebefore cooling to room temperature
  2. concentrationconcentrating in vacuo
  3. customThe crude product was purified by column chromatography (silica)
  4. washeluting with 30% cyclohexane in ethyl acetate
  5. concentrationconcentrated in vacuo
  6. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-83fc0dc278cf45f585b5466307d90732
Source dataset
uspto-grants-2011_07
Patent number
US07985740B2

Reaction notes

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