Methyl chloroformate → HCID 54520631, compound

HRID 1281449Notes

Reaction equation

HRID 1281449 reaction equation
[CH2:1]([NH:13][C:14]([C:16]1[CH:17]=[C:18]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)[C:19]([O:23][CH2:24][CH2:25][NH2:26])=[C:20]([Br:22])[CH:21]=1)=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(N(CC)CC)C.Cl[C:45]([O:47][CH3:48])=[O:46]>C1COCC1>[CH3:48][O:47][C:45](=[O:46])[NH:26][CH2:25][CH2:24][O:23][C:19]1[C:20]([Br:22])=[CH:21][C:16]([C:14](=[O:15])[NH:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:17][C:18]=1[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:34])[F:35])[CH:28]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 53677692HCID 53677692, compound

Product 1

HCID 54520631HCID 54520631, compoundYield 861.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(amino-ethoxy)-5-bromo-3′-trifluoromethyl-biphenyl-3-carboxylic acid dodecylamide (0.273 g, 0.48 mmol, 1 eq) in THF (6 mL) at 0° C. was added triethylamine (0.150 mL, 1.08 mmol, 2.25 eq) followed by methyl chloroformate (0.040 mL, 0.052 mmol, 1.11 eq). The reaction was stirred for 15 min, then poured into pH 7 buffer and extracted with Et2O. The combined organics were dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (30% EtOAc:hexane ) to afford the title compound (0.282 g, 93%) as a white solid. mp 79.6-80.5° C. 1H NMR (DMSO-d6) δ 8.56 (bt, 1H); 8.12 (d, 1H); 7.88 (m, 3H); 7.79 (d, 1H); 7.70 (t, 1H); 7.02 (t, 1H); 3.54 (dd, 2H); 3.44 (s, 3H); 3.24 (dd, 2H); 3.08 (ddd, 2H); 1.48 (dd, 2H); 1.23 (m, 18H); 0.83 (t, 3H); IR (KBr) 3330, 2950, 2840, 1695, 1640, 1540, 1340, 1180, 1110, 920, 805 cm−1; mass spectrum [(+)MAT900], m/z 629/631 (M+H)+; Anal. Calcd. for C30H40BrF3N2O4: C, 57.23; H, 6.40; N, 4.45, Found: C, 56.12; H, 6.29; N, 4.29.

Workup

  1. additionpoured into pH 7 buffer
  2. extractionextracted with Et2O
  3. dry with materialThe combined organics were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (30% EtOAc:hexane )

Sources & evidence

ORD record
ord-41ca03bcca4349978d3dada2ee198433
Source dataset
uspto-grants-2002_09
Patent number
US06451827B2

Reaction notes

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