Triethylamine → HCID 11759569, compound

HRID 392901Notes

Reaction equation

HRID 392901 reaction equation
C(N(CC)CC)C.[CH3:8][NH:9][C:10]([C@@H:12]1[C@@H:16]([N:17]=[N+:18]=[N-:19])[C@@H:15]([O:20]C(=O)C)[C@H:14]([N:24]2[CH:32]=[N:31][C:30]3[C:25]2=[N:26][CH:27]=[N:28][C:29]=3[Cl:33])[O:13]1)=[O:11]>CO>[CH3:8][NH:9][C:10]([C@@H:12]1[C@@H:16]([N:17]=[N+:18]=[N-:19])[C@@H:15]([OH:20])[C@H:14]([N:24]2[CH:32]=[N:31][C:30]3[C:25]2=[N:26][CH:27]=[N:28][C:29]=3[Cl:33])[O:13]1)=[O:11]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 11675322HCID 11675322, compound

Product 1

HCID 11759569HCID 11759569, compoundYield 72,467.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triethylamine (4.4 mL, 0.032 mL) was added to a solution of (2S,3S,4R,5R)3-azido-5-(6-chloro-purin-9-yl)-4-acetoxy-tetrahydro-furan-2-carboxylic acid methylamide (4 g, 0.011 mmol) in methanol (80 mL). After stirring for 15 hours, the mixture was concentrated and the residue purified by flash chromatography (5% methanol/dichloromethane) to afford 2.7 g (77%) of the title compound as a colorless solid. MS 339 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 8.72 (s, 1H); 8.2 (s, 1H); 7.62 (bs, 1H); 5.98 (d, 1H, J=6.7 Hz); 5.07 (t, 1H, J=6.2 Hz); 4.65 (dd, 1H, J=5.4, 2.7 Hz); 4.58 (m, 1H); 4.2 (bs, 1H); 2.88 (d, 1H, J=4.9 Hz); 1.67 (bs, 1H).

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue purified by flash chromatography (5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-e601958c6c5549a0988deb1bc866994f
Source dataset
uspto-grants-2004_10
Patent number
US06803457B1

Reaction notes

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