Isopropyl chloroformate → HCID 18182587, compound

HRID 1359603Notes

Reaction equation

HRID 1359603 reaction equation
C(C[CH:5]1[C:9]2[CH:10]=[C:11]([C:14]#[N:15])[CH:12]=[CH:13][C:8]=2[O:7][CH2:6]1)(O)=O.C(N(CC)CC)C.ClC([O:26][CH:27](C)[CH3:28])=O.Cl.[NH2:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:35][CH:34]=1>C(Cl)Cl>[C:36]1([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:37]=[CH:38][C:33]([CH2:32][NH:31][C:27](=[O:26])[CH2:28][CH:6]2[CH2:5][C:9]3[CH:10]=[C:11]([C:14]#[N:15])[CH:12]=[CH:13][C:8]=3[O:7]2)=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 7917Isopropyl chloroformateHCID 8471Triethylamine2×HCID 181825291-([1,1'-Biphenyl]-4-yl)methanamine--hydrogen chloride (1/1)HCID 18182548HCID 18182548, compound

Product 1

HCID 18182587HCID 18182587, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) suspension of 3-(carboxy-methyl)-5-cyano-2,3-dihydrobenzofuran (300 mg, 1.5 mmol, reference example 9) in CH2Cl2 (4 mL) is added triethylamine (210 mL, 1.5 mmol) followed by isopropyl chloroformate (1.65 mL, 1 M in CH2Cl2). The resulting solution is stirred for 20 min then a further portion of triethylamine is added (455 mL, 3.3 mmol) followed by 4-aminomethyl biphenyl hydrochloride (330 mg, 1.5 mmol). The cold bath is removed and stirring continued for 5 h. The reaction mixture is then diluted with CH2Cl2, washed with water and brine, dried over MgSO4 and concentrated. The residue was triturated with ether and the solid filtered to give 400 mg of the title compound. 1H NMR (CDCl3) δ2.55 (dd, J=16, 8 Hz, 1H), 2.65 (dd, J=16, 6 Hz, 1H), 4.06 (m, 1H), 4.42 (dd, J=8, 7 Hz, 1H), 4.49 (dd, J=15, 6 Hz, 1H), 4.55 (dd, J=15, 6 Hz, 1H), 4.88 (t, J=8 Hz, 1H), 6.83 (m, 1H), 7.38 (m, 3H), 7.37 (m, 1H), 7.45 (m, 4H), 7.61 (m, 4H). MS (EI) m/z 368 (M+).

Workup

  1. temperatureTo a cooled
  2. customThe cold bath is removed
  3. stirringstirring
  4. waitcontinued for 5 h
  5. additionThe reaction mixture is then diluted with CH2Cl2
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was triturated with ether
  10. filtrationthe solid filtered

Sources & evidence

ORD record
ord-c5bd0d258b3d428b93d4b6e0f312d7e5
Source dataset
uspto-grants-2003_07
Patent number
US06599918B2

Reaction notes

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