Methyl chloroformate → HCID 67508140, compound

HRID 1400041Notes

Reaction equation

HRID 1400041 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[C:10]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:24][C@H:23]([CH2:25][NH2:26])[O:22][C:21]4=[O:27])=[CH:16][CH:15]=3)([CH2:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:36]([O:38][CH3:39])=[O:37]>C1COCC1.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[C:10]([C:14]3[CH:15]=[CH:16][C:17]([N:20]4[CH2:24][C@H:23]([CH2:25][NH:26][C:36]([O:38][CH3:39])=[O:37])[O:22][C:21]4=[O:27])=[CH:18][CH:19]=3)([CH2:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 67509560HCID 67509560, compound

Product 1

HCID 67508140HCID 67508140, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of solution of compound (400 mg, 1.1 mmol) obtained in Step 1, in THF (20 mL) was added triethylamine (0.45 mL, 3.2 mmol). The resulting solution was cooled to 0° C. and methyl chloroformate (0.12 mL, 1.6 mmol) was added dropwise. The reaction mixture was stirred at r.t. and progress of the reaction was monitored by TLC. On completion, the reaction mixture was diluted with DCM (60 mL). The organic layer was washed with water (25 mL), brine (25 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 2:8 EtOAc:Pet. ether) to provide the title compound (320 mg, 70%) as white solid.

Workup

  1. washThe organic layer was washed with water (25 mL), brine (25 mL)
  2. dry with materialdried over anhydrous sodium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography (silica gel, 2:8 EtOAc:Pet. ether)

Sources & evidence

ORD record
ord-b7e412378651428d81d16463a7c3f2c6
Source dataset
uspto-grants-2014_12
Patent number
US08906913B2

Reaction notes

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