Ethyl chloroformate → HCID 69322566, compound

HRID 448091Notes

Reaction equation

HRID 448091 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9](=[O:22])/[CH:10]=[C:11]1\[S:12][C:13]([CH3:21])=[C:14]([CH3:20])[N:15]\1[CH2:16][CH2:17][CH2:18][CH3:19].C([O-])(O)=O.[Na+].Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30]>CCOC(C)=O.O>[CH2:16]([N:15]1[C:14]([CH3:20])=[C:13]([CH3:21])[S:12]/[C:11]/1=[CH:10]\[C:9]([C:3]1[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=1[NH:1][C:29](=[O:30])[O:31][CH2:32][CH3:33])=[O:22])[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 69166813HCID 69166813, compound

Product 1

HCID 69322566HCID 69322566, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of Example 139 (17 mg, 0.05 mmol) and NaHCO3 (42 mg, 0.5 mmol) in EtOAc (5 mL) and H2O (5 mL) was added dropwise at room temperature a solution of ethyl chloroformate (0.06 mL, 0.06 mmol) in EtOAc (3 mL) and the reaction was continued for the next 4 h. The ethyl acetate layer was separated, washed with brine, dried with anhydrous MgSO4 and concentrated under reduced pressure. The residue was chromatographed (EtOAc as eluent) to afford 20 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 0.94 (t, J=7 Hz, 3H), 1.24 (t, J=7 Hz, 3H), 1.37 (sextet, J=7 Hz, 2H), 1.62 (quintet, J=7 Hz, 2H), 2.10 (s, 3H), 2.14 (s, 3H), 4.13 (m, 4H), 6.56 (s, 1H), 7.42 (dd, J=9 Hz, 3 Hz, 1H), 7.96 (d, J=3 Hz, 1H 8.23 (d, J=9 Hz, 1H), 11.98 (s, 1H); MS (DCI/NH3) m/z 409 (M+H)+. Anal calcd for C20H25ClN2O3S: C, 58.74; H, 6.16; N, 6.85. Found: C, 59.02; H, 5.98; N, 6.31.

Workup

  1. customwas continued for the next 4 h
  2. customThe ethyl acetate layer was separated
  3. washwashed with brine
  4. dry with materialdried with anhydrous MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed (EtOAc as eluent)

Sources & evidence

ORD record
ord-3aa444ff234b469aad60d5aff36585ee
Source dataset
uspto-grants-2013_07
Patent number
US08481574B2

Reaction notes

Loading…