Benzyl chloroformate → HCID 67951139, compound

HRID 923644Notes

Reaction equation

HRID 923644 reaction equation
[O:1]=[C:2]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)[CH2:3][N:4]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[S:5]1.Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22].CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[O:9]=[C:8]1[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[S:5][N:4]1[CH2:3][C:2]([N:14]1[CH2:19][CH2:18][N:17]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:16][CH2:15]1)=[O:1]

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 67813078HCID 67813078, compound

Product 1

HCID 67951139HCID 67951139, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 10 (100 mg, 0.36 mmol) was treated with benzyl chloroformate (75 mg, 0.44 mmol) and DIEA (140 mg, 1.10 mmol) in anhydrous CH2Cl2 (5 mL) and DMF (1 mL) at room temperature for 4 h. CH2Cl2 and DMF were removed in reduced pressure. The mixture was washed successively with 1 M HCl(aq) and saturated NaHCO3(aq.). The organic phase was dried over MgSO4, filtered, concentrated, and the title compound was obtained after purification on a thin-layer silica-gel plate (20 cm×20 cm×2 mm) using CH2Cl2/MeOH (9:1) as the developing solution. C21H21N3O4S; white solid; mp 138-142° C.; IR vmax (neat) 2923, 2854, 1700, 1655, 1428, 1354, 1286, 1227, 1125, 1075, 1027, 984, 861, 741 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.01 (1H, d, J=8.0 Hz), 7.60 (1H, t, J=7.2 Hz), 7.53 (1H, d, J=8.0 Hz), 7.36 (6H, m), 5.12 (2H, s), 4.69 (2H, s), 3.62 (8H, m); 13C NMR (100 MHz, CDCl3) δ 165.1, 154.8, 141.1, 136.1, 132.1, 128.5, 128.1, 127.9, 126.7 (2×), 126.3 (2×), 125.4, 123.2, 120.2, 67.6, 45.2, 44.9, 43.6 (2×), 42.0; ESI-HRMS calcd for C21H21N3O4NaS: 434.1150. found: m/z 434.1149 [M+H]+.

Workup

  1. customCH2Cl2 and DMF were removed in reduced pressure
  2. washThe mixture was washed successively with 1 M HCl(aq) and saturated NaHCO3(aq.)
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6333bbd3a808422fbded8cfead45f7f1
Source dataset
uspto-grants-2016_03
Patent number
US09278982B2

Reaction notes

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