Trifluoroacetic acid → HCID 58944647, compound

HRID 222208Notes

Reaction equation

HRID 222208 reaction equation
C(OC(=O)[N:7]([S:34]([NH2:37])(=[O:36])=[O:35])[CH2:8][C@@H:9]1[CH2:13][C@@H:12]([N:14]2[C:18]3[N:19]=[CH:20][N:21]=[C:22]([NH:23][C@@H:24]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH2:26][CH2:25]4)[C:17]=3[CH:16]=[CH:15]2)[CH2:11][C@@H:10]1[OH:33])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.C1(C)C=CC=CC=1>[C@@H:24]1([NH:23][C:22]2[C:17]3[CH:16]=[CH:15][N:14]([C@@H:12]4[CH2:13][C@@H:9]([CH2:8][NH:7][S:34]([NH2:37])(=[O:36])=[O:35])[C@@H:10]([OH:33])[CH2:11]4)[C:18]=3[N:19]=[CH:20][N:21]=2)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58944555HCID 58944555, compound

Product 1

HCID 58944647HCID 58944647, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl(aminosulfonyl)[((1S,2S,4R)-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-hydroxycyclopentyl)methyl]carbamate (345 mg, 0.000636 mol) was dissolved in 2:1 methylene chloride:trifluoroacetic acid (20 mL: 10 mL) and left to stand for 15 minutes at room temperature. The mixture was diluted with toluene (30 mL) and evaporated to dryness. The residue was then re-subjected to the same conditions and azeotroped with toluene after completion. The residue was purified by silica gel chromatography, eluting with 5 to 10% Methanol in dichloromethane, to yield the product, 135 mg (48%). 1H-NMR (400 MHz, MeOD) δ 8.16 (s, 1H), 7.19 (m, 5H), 6.62 (d, J=3.6 Hz, 1H), 5.85 (t, J=7.8 Hz, 1H) 5.43 (ddd, J=4.6 Hz, 8.5 Hz, 17.8 Hz, 1H), 4.46 (t, J=3.6 Hz, 1H), 3.15 (dd, J=7.1 Hz, 12.9 Hz, 1H), 3.05 (ddd, J=3.3 Hz, 8.7 Hz, 15.4 Hz, 1H), 2.91 (m, 1H), 2.63 (m, 1H), 2.33 (ddd, J=1.5 Hz, 8.0 Hz, 13.8 Hz, 1H), 2.20 (m, 2H), 2.02 (m, 2H). LC/MS: Rt=1.45 min, ES+ 443 (AA standard).

Workup

  1. customevaporated to dryness
  2. customazeotroped with toluene after completion
  3. customThe residue was purified by silica gel chromatography
  4. washeluting with 5 to 10% Methanol in dichloromethane
  5. customto yield the product, 135 mg (48%)

Sources & evidence

ORD record
ord-f00652b726ba472398705edfccf13695
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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