Water → HCID 57308030, compound

HRID 1417020Notes

Reaction equation

HRID 1417020 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[CH2:15][C:14]([CH2:16][OH:17])=[CH:13][CH2:12]2)=[C:4]([Cl:18])[N:3]=1.C[N+]1([O-])CC[O:23]CC1.C(O)(C)(C)C.[OH2:32]>[Os](=O)(=O)(=O)=O>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:12][C@H:13]([OH:32])[C@:14]([CH2:16][OH:17])([OH:23])[CH2:15]2)=[C:4]([Cl:18])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 54566808HCID 54566808, compound

Product 1

HCID 57308030HCID 57308030, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

(4R)-4-(2-Amino-6-chloro-9H-purin-9-yl)-1-cyclopentene-1-methanol (Part b, 501 mg, 1.89 mmol), N-methylmorpholine N-oxide (60% aqueous solution, Aldrich, 0.33 mL, 1.89 mmol), osmium tetroxide (2.5% in t-butyl alcohol Aldrich, 0.47 mL), and t-butyl alcohol (12 mL) were heated at 60° C. for 1.5 hours. Volaties were evaporated and the residual solids were chromatographed on silica gel. Title compound was eluted with 10% methanol-chloroform as tan solid (210 mg) and resolidified from absolute ethanol to give white powder, m.p. 217-219° C.; mass spectrum (Cl/CH4): 302, 300 (M+1), 172, 170 (B+H); 1H-NMR (DMSO-d6)δ: 8.29 (s, 1, purine CH), 6.9 (br s, 2, NH2), 5.15-4.90 (m, 1, NCH), 4.80 (d, J=3.9 Hz) overlapping 4.78 (t, J=3.5 Hz, total 2, 2 OH), 4.30 (s) overlapping 4.3-4.2 (m, total 2, OH and OCH), 3.45-3.35 (m, overlapping water, CH2OH), 2.25-2.05 (m, 4,2 CH2).

Workup

  1. customVolaties were evaporated
  2. customthe residual solids were chromatographed on silica gel
  3. washTitle compound was eluted with 10% methanol-chloroform as tan solid (210 mg)
  4. customto give white powder, m.p. 217-219° C.

Sources & evidence

ORD record
ord-dc1c151c24b5458abe355a00eb74d777
Source dataset
uspto-grants-1999_06
Patent number
US05917042

Reaction notes

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