HCID 86618730, compound → HCID 86618731, compound

HRID 1397598Notes

Reaction equation

HRID 1397598 reaction equation
[S:1](=[O:39])(=[O:38])([O:3][CH2:4][C@@H:5]1[CH2:9][C@@H:8]([O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C@@H:18]3[C:26]4[C:21](=[CH:22][C:23]([Cl:27])=[CH:24][CH:25]=4)[C:20]([CH3:29])([CH3:28])[CH2:19]3)[CH:12]=2)[CH2:7][C@@H:6]1[O:30][Si](C(C)(C)C)(C)C)[NH2:2]>Cl.C(O)C>[S:1](=[O:39])(=[O:38])([O:3][CH2:4][C@@H:5]1[CH2:9][C@@H:8]([O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C@@H:18]3[C:26]4[C:21](=[CH:22][C:23]([Cl:27])=[CH:24][CH:25]=4)[C:20]([CH3:28])([CH3:29])[CH2:19]3)[CH:12]=2)[CH2:7][C@@H:6]1[OH:30])[NH2:2]

Participants

4

Reactant 1

HCID 86618730HCID 86618730, compound

Product 1

HCID 86618731HCID 86618731, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of {(1S,2S,4R)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-[(2-{[(1S)-5-chloro-3,3-dimethyl-2,3-dihydro-1H-inden-1-yl]amino}pyridin-4-yl)oxy]cyclopentyl}methyl sulfamate (0.0287 g, 0.0000481 mol) in 3.0% (V/V) HCl in ethanol (25.0 ml) was stirred for 4 hrs. The reaction was concentrated and dissolved in 50 ml EtOAc and 1.00 ml triethylamine. The solution was washed with water, concentrated, and the residue was isolated by preparative plate chromatography (5% MeOH/EtOAc) to afford the title compound (16.5 mg, 71%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ: 7.92 (d, 1H, J=5.8 Hz), 7.22-7.20 (m, 1H), 7.17-7.14 (m, 2H), 6.16 (dd, 1H, J=6.0 Hz, J=2.3 Hz) 5.85 (d, 1H, J=2.0 Hz), 5.30 (m, 1H), 4.92 (m, 1H), 4.70 (d, 1H, J=8.5 Hz), 4.50 (dt, 1H, J=5.0 Hz, J=1.9 Hz), 4.40 (dd, 1H, J=7.3 Hz, J=2.5 Hz), 4.28 (dd, 1H, J=7.3 Hz, J=2.5 Hz), 2.60 (bs, 1H), 2.50 (q, 1H, J=7.0 Hz), 2.31-2.25 (m, 1H), 2.18-2.12 (m, 1H), 1.95-1.87 (m, 2H), 1.79 (m, 1H), 1.25 (s, 6H). LC/MS: Rt=1.81 min, ES+ 482 (AA standard).

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in 50 ml EtOAc
  3. washThe solution was washed with water
  4. concentrationconcentrated
  5. customthe residue was isolated by preparative plate chromatography (5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-65d2d2cbfac0435e948e7bd0ec901a67
Source dataset
uspto-grants-2014_12
Patent number
US08901136B2

Reaction notes

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