Acetic Acid → (2R,3S)-diethyl 2-((5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-3-hydroxysuccinate

HRID 533208Notes

Reaction equation

HRID 533208 reaction equation
[NH2:1][C@H:2]([C@H:8]([OH:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C([BH3-])#N.[Na+].[CH2:19]([O:26][CH2:27][N:28]1[C:36]2[C:35]([O:37][CH3:38])=[N:34][CH:33]=[N:32][C:31]=2[C:30]([CH:39]=O)=[CH:29]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O)(=O)C>CO>[CH2:19]([O:26][CH2:27][N:28]1[C:36]2[C:35]([O:37][CH3:38])=[N:34][CH:33]=[N:32][C:31]=2[C:30]([CH2:39][NH:1][C@H:2]([C@H:8]([OH:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:29]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 10845890(2R,3S)-diethyl 2-amino-3-hydroxysuccinateHCID 577250835-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidine-7-carbaldehyde

Product 1

HCID 25223389(2R,3S)-diethyl 2-((5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-3-hydroxysuccinateYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of (2R,3S)-diethyl 2-amino-3-hydroxysuccinate (prepared as described in A. Breuning, R. Vicik and T. Schirmeister, Tetrahedron Asymm., 2003, 14, 3301 and Z. Tang, Z.-H. Yang, X.-H. Chen, L.-F. Cun, A.-Q. Mi, Y.-Z. Jiang and L.-Z. Gong, J. Am. Chem. Soc., 2005, 127, 9285) (0.109 g, 0.53 mmol), sodium cyanoborohydride (0.055 g, 0.88 mmol) and 5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-carbaldehyde (0.131 g, 0.44 mmol) were evaporated from methanol (3×). The residue was dissolved in methanol (10 ml) and acetic acid added (5 drops). The reaction mixture was stirred at ambient temperature for 2 h. The reaction mixture was evaporated on to silica gel and chromatographed (ethyl acetate-petrol, 2:1 then ethyl acetate-triethylamine, 1:99) giving a colourless oil (0.166 g, 77%). 1H NMR (CDCl3) δ 8.55 (s, 1H), 7.34 (s, 1H), 7.33-7.23 (m, 5H); 5.70 (s, 2H), 4.62 (d, J=3.4 Hz, 1H), 4.48 (s, 2H), 4.23-4.15 (m, 5H), 4.10 (s, 3H), 3.99 (d, J=13.8 Hz, 1H), 3.85 (d, J=2.3 Hz, 1H), 2.25 (brs, 2H), 1.26 (t, J=7.1 Hz, 3H), 1.25 (t, J=7.1 Hz, 3H).

Workup

  1. customprepared
  2. customThe reaction mixture was evaporated on to silica gel
  3. customchromatographed (ethyl acetate-petrol, 2:1

Sources & evidence

ORD record
ord-685317b82cb64833a7594143d566e8c2
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

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