Triethylamine hydrochloride → HCID 135858785, compound

HRID 533224Notes

Reaction equation

HRID 533224 reaction equation
[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[N:4]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:3]1[C:17]1[C:21]2[N:22]=[CH:23][N:24]=[C:25]([OH:26])[C:20]=2[NH:19][CH:18]=1.Cl.C(N(CC)CC)C.I([O-])(=O)(=O)=O.[Na+].[BH4-].[Na+]>CO.O>[OH:9][CH2:8][CH:5]([N:4]([C@@H:3]([C:17]1[C:21]2[N:22]=[CH:23][NH:24][C:25](=[O:26])[C:20]=2[NH:19][CH:18]=1)[CH2:2][OH:1])[C:10](=[O:11])[O:12][C:13]([CH3:15])([CH3:16])[CH3:14])[CH2:6][OH:7]

Participants

7

Reactant 4

HCID 11130Triethylamine hydrochlorideHCID 4311764Sodium borohydrideHCID 23667635Sodium periodateHCID 178452535HCID 178452535, compound

Product 1

HCID 135858785HCID 135858785, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Di-tert-butyl Bicarbonate (0.091 g, 0.416 mmol) was added to a solution of (2S,3S,4R,5R)-2-(4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-5-(hydroxymethyl)pyrrolidine-3,4-diol hydrochloride (0.07 g, 0.231 mmol, synthesized according to G. B. Evans, R. N. Furneaux, G. J. Gainsford, V. L. Schramm and P. C. Tyler, Tetrahedron, 2000, 56, 3053) and triethylamine (0.065 ml, 0.462 mmol) in a mixture of water (1 ml) and MeOH (3 ml). The solution was stirred for 30 mins., then the solvent evaporated to give 116 mg of a colourless solid which consisted, as estimated by 1H NMR, of about 78 mg, 0.213 mmol of (2S,3S,4R,5R)-tert-butyl 3,4-dihydroxy-2-(4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate with the rest being triethylamine hydrochloride. This mixture was dissolved in MeOH (4 ml) and water (3 nil) and sodium periodate (0.055 g, 0.255 mmol) added. After stirring for 15 mins a precipitate formed. Sodium borohydride (0.024 g, 0.639 mmol) was added and the mixture stirred for 15 mins then filtered through Celite and the solvent evaporated. The residue was chromatographed on silica gel (CH2Cl2-MeOH, 85:15) to give (S)-tert-butyl 1,3-dihydroxypropan-2-yl(2-hydroxy-1-(4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-7-yl)ethyl)carbamate (0.072 g, 92%) as a colourless solid. 1H NMR (CD3OD) δ 7.89 (s, 1H), 7.50 (br.s 1H), 5.32 (br. s, 0.5 H), 5.08 (br. s, 0.5H), 4.28 (br.s 1H), 4.17-3.50 (br. m, 6H), 1.39 (br. d, 9H). +ESMS Found 369.1760 (M+H)+ C16H25N4O6 requires 369.1774. [α]D20 +35.8 (c, 0.505, MeOH).

Workup

  1. customformed
  2. stirringthe mixture stirred for 15 mins
  3. filtrationthen filtered through Celite
  4. customthe solvent evaporated
  5. customThe residue was chromatographed on silica gel (CH2Cl2-MeOH, 85:15)

Sources & evidence

ORD record
ord-60f9626c7f2d4665a9c4ff5615ca4377
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

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