Triethylamine → HCID 59485870, compound

HRID 1972197Notes

Reaction equation

HRID 1972197 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C@H:16]([CH2:24][NH2:25])[O:15][C:14]3=[O:26])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[S:36](Cl)([CH3:39])(=[O:38])=[O:37]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C@H:16]([CH2:24][NH:25][S:36]([CH3:39])(=[O:38])=[O:37])[O:15][C:14]3=[O:26])=[CH:11][CH:12]=2)=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59485942HCID 59485942, compound

Product 1

HCID 59485870HCID 59485870, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4S,5S)-3-(4-(4-chlorophenoxy)phenyl)-5-(aminomethyl)-4-phenyl-oxazolidin-2-one (14 mg, 0.035 mmol) and triethylamine (0.01 mL, 0.07 mmol) in dichloromethane (0.4 mL) at 0° C. was added mesyl chloride (0.005 mL, 0.05 mmol). The reaction mixture was stirred for 10 min and was then quenched with saturated NaHCO3 aqueous solution. Water and dichloromethane was added and the organic was washed with brine, dried (MgSO4), and concentrated. Purification by prep-LC (10-90% Acetonitrile/water (0.05% ammonium acetate) gave 5 mg (31%). 1H NMR (acetone-d6) δ (ppm) 7.45-7.51 (m, 4H), 7.32-7.42 (m, 5H), 6.94-6.97 (m, 4H), 6.66 (t, 1H, J=6.6 Hz), 5.56 (d, 1H, J=5.6 Hz), 4.51, (dd, 1H, J=10.1, 4.7 Hz), 3.59-3.72 (m, 2H), 3.04 (s, 3H). HPLC-MS calculated C23H21ClN2O5S (M+H+): 473.1, found: 473.1.

Workup

  1. customwas then quenched with saturated NaHCO3 aqueous solution
  2. additionWater and dichloromethane was added
  3. washthe organic was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification by prep-LC (10-90% Acetonitrile/water (0.05% ammonium acetate)
  7. customgave 5 mg (31%)

Sources & evidence

ORD record
ord-49461c46b338422aa2770d79479cb1c6
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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