Hydrochloric Acid → HCID 69423716, compound

HRID 914728Notes

Reaction equation

HRID 914728 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][C@H:8]([NH:11][C:12]1[N:20]=[CH:19][N:18]=[C:17]2[C:13]=1[N:14]=[CH:15][N:16]2[C@H:21]1[C@H:28]2[C@H:24]([O:25]C(C)(C)[O:27]2)[C@@H:23]([CH2:31][F:32])[CH2:22]1)[CH2:9][CH3:10].Cl.O>C1COCC1.O(C(C)C)C(C)C.CCCCC>[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][C@H:8]([NH:11][C:12]1[N:20]=[CH:19][N:18]=[C:17]2[C:13]=1[N:14]=[CH:15][N:16]2[C@@H:21]1[CH2:22][C@H:23]([CH2:31][F:32])[C@@H:24]([OH:25])[C@H:28]1[OH:27])[CH2:9][CH3:10]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 69433361HCID 69433361, compound

Product 1

HCID 69423716HCID 69423716, compound

Reagents, catalysts & solvents 3

HCID 7914Diisopropyl EtherSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

[(R)-1-(3-chloro-thiophen-2-ylmethyl)-propyl]-[9-((3aS,4R,6S,6aR)-6-fluoromethyl-2,2-dimethyl-tetrahydro-cyclopenta-1,3-dioxol-4-yl)-9H-purin-6-yl]-amine (1.23 g, 2.56 mmoles) prepared as described above was put in solution in THF (31 ml) and the resulting solution was treated with 12 N HCl in water (2.56 ml, 30.7 mmoles), and stirred for 2 h at room temperature. The solvent was then evaporated to dryness and the residue partitioned between water and AcOEt and neutralized with a saturated bicarbonate solution, the aqueous layer was separated and extracted twice with EtOAc. The combined organic layers were washed with brine and dried over sodium sulfate. The filtrate was concentrated under reduced pressure to give a residue which was taken up in iPr2O and the resulting solution is diluted with pentane, the solid was filtrated, washed with pentane 3 times and dried to yield (1R,2S,3R,5S)-3-{6-[(R)-1-(3-chloro-thiophen-2-ylmethyl) -propylamino]-purin-9-yl}-5-fluoromethyl-cyclopentane-1,2-diol. 1H NMR (300 MHz, (CD3)2SO d6, δ in ppm): 0.92 (t, J=7,5 Hz: 3H); 1.68 (mt: 2H); 1.84 (mt: 1H); 2.31 (mt:2H); 3.13 (mt:2H); 3.92 (mt: 1H); 4.40 (mt: 1H); 4.51 (mf: 1H); 4.55 (dmt, JHF=48 Hz: 2H); 4.75 (mt: 1H); 4.94 (d, J=3,5 Hz: 1H); 5.10 (d, J=6 Hz: 1H); 6.98 (d, J=5 Hz: 1H); 7.43 (d, J=5 Hz: 1H); 7.72 (broad d, J=8 Hz: 1H); 8.18 (mf: 1H); 8.23 (s:1H). m.p.=143°.

Workup

  1. customThe solvent was then evaporated to dryness
  2. customthe residue partitioned between water and AcOEt
  3. customthe aqueous layer was separated
  4. extractionextracted twice with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customto give a residue which
  9. filtrationthe solid was filtrated
  10. washwashed with pentane 3 times
  11. customdried

Sources & evidence

ORD record
ord-752c335d14ec43268bf06414b2b7f8bf
Source dataset
uspto-grants-2007_09
Patent number
US07265111B2

Reaction notes

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