Ammonia → HCID 68774486, compound

HRID 1175668Notes

Reaction equation

HRID 1175668 reaction equation
C[O:2][C:3]([C:5]1[N:9]=[CH:8][N:7]([CH:10]2[CH:14]([O:15]C(=O)C3C=CC=CC=3)[CH2:13][CH:12]([O:24][CH2:25][P:26]([O:31]CC)([O:28]CC)=[O:27])[O:11]2)[N:6]=1)=O.Br[Si](C)(C)C.[N:39]1C(C)=CC=CC=1C.N>CC#N>[C:3]([C:5]1[N:9]=[CH:8][N:7]([CH:10]2[O:11][CH:12]([O:24][CH2:25][P:26](=[O:27])([OH:28])[OH:31])[CH2:13][CH:14]2[OH:15])[N:6]=1)(=[O:2])[NH2:39]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 79372,6-LutidineHCID 76113BromotrimethylsilaneHCID 72326310HCID 72326310, compound

Product 1

HCID 68774486HCID 68774486, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The 1-[3-benzoyloxy-5-(diethoxy-phosphorylmethoxy)-tetrahydrofuran-2-yl]-1H-[1,2,4]triazole-3-carboxylic acid methyl ester (60 mg. 0.124 mmol) was dissolved in MeCN (1.5 mL). Bromotrimethylsilane (0.164 mL, 1.24 mmol) and 2,6-lutidine (0.043 mL, 0.372 mmol) were added and the mixture stirred at ambient temperature for 10 h. The solvents were removed in vacuo and the product isolated by C-18 HPLC. To this was then added ammonia (7 N in MeOH, 4 mL) and the mixture stirred overnight. The title compound was isolated by C-18 HPLC. 1H NMR (300 MHz, D2O) ppm 8.65 (s, 1H), 5.95 (d, 1H, J=2.4 Hz), 5.49-5.52 (m, 1H), 4.81-4.89 (m, 1H), 3.47-3.70 (m, 2H), 2.27-2.32 (m, 2H). 31P NMR (121.4 MHz, D2O) ppm 15.0. LRMS (ESI) M-H C8H12N4O7P requires 307.0 Found 307.0.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe product isolated by C-18 HPLC

Sources & evidence

ORD record
ord-005559563f9a474d969f45d50d53ed90
Source dataset
uspto-grants-2010_11
Patent number
US07842672B2

Reaction notes

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