Methanesulfonyl chloride → HCID 58909420, compound

HRID 1985050Notes

Reaction equation

HRID 1985050 reaction equation
[NH2:1][C@@H:2]([CH2:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=1)[C@H:3]([OH:17])[CH2:4][NH:5][C@@H:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([I:16])[CH:14]=2)[O:9][CH2:8][CH2:7]1.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[F:25][C:23]1[CH:24]=[C:19]([CH:20]=[C:21]([F:26])[CH:22]=1)[CH2:18][C@H:2]([NH:1][S:28]([CH3:27])(=[O:30])=[O:29])[C@H:3]([OH:17])[CH2:4][NH:5][C@@H:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([I:16])[CH:14]=2)[O:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 58909298HCID 58909298, compound

Product 1

HCID 58909420HCID 58909420, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-{[(4S)-6-iodo-3,4-dihydro-2H-chromen-4-yl]amino}butan-2-ol (1 equiv) was dissolved in DCM with TEA (2 equiv) then cooled to 0° C. and treated with MsCl (1.25 equiv)while stirring. The reaction mixture was removed from the cold bath, brought to ambient temperature, then quenched with MeOH and concentrated. The residue was dissolved in EtOAc and washed with 1M HCl (2×10 mL). The organics were dried and concentrated and chromatographed over silica gel. 1H NMR (CD3OD) δ 7.74 (d, J=2.0 Hz, 1 H), 7.53 (dd, J=2.0, 8.7 Hz, 1 H), 6.88 (m, 2 H), 6.77 (m, 1 H), 6.67 (d, J=8.7 Hz, 1 H), 4.23-4.39 (m, 2 H), 4.25 (br m, 1 H), 4.12 (m, 1 H), 3.87 (td, J=3.1, 7.8 Hz, 1 H), 3.29 (dd, J=3.5, 13.9 Hz, 1 H), 3.11 (s, 3H), 3.05 (dd, J=3.2, 12.7 Hz, 1 H), 2.98 (dd, J=7.9, 12.6 Hz, 1 H), 2.74 (dd, J=11.0, 13.9 Hz, 1 H), 2.14 (br m, 2 H). MS (ESI+) calcd for C20H23F2IN2O4S m/z 553.38 (M+H)+. Found 553.4.

Workup

  1. customThe reaction mixture was removed from the cold bath
  2. custombrought to ambient temperature
  3. customquenched with MeOH
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in EtOAc
  6. washwashed with 1M HCl (2×10 mL)
  7. customThe organics were dried
  8. concentrationconcentrated
  9. customchromatographed over silica gel

Sources & evidence

ORD record
ord-69715d8109e84d5f94376a320ace4946
Source dataset
uspto-grants-2009_06
Patent number
US07544717B2

Reaction notes

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