HCID 86614249, compound → HCID 86614248, compound

HRID 222164Notes

Reaction equation

HRID 222164 reaction equation
[S:1](=[O:32])(=[O:31])([O:3][CH2:4][C@@H:5]1[C@@H:12]2[C@@H:8]([O:9]C(C)(C)[O:11]2)[C@H:7]([N:15]2[C:19]3[N:20]=[CH:21][N:22]=[C:23]([S:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:18]=3[CH:17]=[CH:16]2)[CH2:6]1)[NH2:2]>FC(F)(F)C(O)=O.O>[S:1](=[O:32])(=[O:31])([O:3][CH2:4][C@H:5]1[CH2:6][C@@H:7]([N:15]2[C:19]3[N:20]=[CH:21][N:22]=[C:23]([S:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:18]=3[CH:17]=[CH:16]2)[C@H:8]([OH:9])[C@@H:12]1[OH:11])[NH2:2]

Participants

4

Reactant 1

HCID 86614249HCID 86614249, compound

Product 1

HCID 86614248HCID 86614248, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

{(3aR,4R,6R,6aS)-2,2-Dimethyl-6-[4-(phenylsulfanyl)-7H-pyrrolo[2,3-d]-pyrimidin-7-yl]tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}methyl sulfamate (14.4 mg, 30.2 mmol) was stirred in 1.00 mL of 90% trifluoroacetic acid in water for 3 h at rt. The solvent was then removed in vacuo and the resulting oil was purified by silica gel chromatography eluting with a gradient of 60 to 100% EtOAc in hexanes to afford the title compound (7.50 mg, 57%). 1H NMR (400 MHz, CD3OD, δ): 8.45 (s, 1H), 7.66-7.36 (m, 2H), 7.51-7.41 (m, 4H), 5.92 (d, J=3.8 Hz, 1H), 5.13-5.06 (m, 1H), 4.58-4.55 (dd, J=3.8, 9.0 Hz, 1H), 4.42-4.37 (dd, J=8.0, 9.8 Hz, 1H), 4.18-4.14 (m, 2H), 2.92-2.82 (m, 1H), 2.24-2.08 (m, 2H) ppm. LC/MS: Rt=1.38 min, ES+ 437 (FA standard).

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe resulting oil was purified by silica gel chromatography
  3. washeluting with a gradient of 60 to 100% EtOAc in hexanes

Sources & evidence

ORD record
ord-4d720c5b8c6341a1b40a152a51234753
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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