Methyl chloroformate → HCID 23648642, compound

HRID 404884Notes

Reaction equation

HRID 404884 reaction equation
[CH:1]([O:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:20]=[C:19]([CH:21]([NH2:23])[CH3:22])[O:18][N:17]=3)=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].Cl[C:27]([O:29][CH3:30])=[O:28]>O1CCCC1.C(N(CC)CC)C.ClCCl>[CH:1]([O:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:20]=[C:19]([CH:21]([NH:23][C:27](=[O:28])[O:29][CH3:30])[CH3:22])[O:18][N:17]=3)=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 6586Methyl chloroformateHCID 69435781HCID 69435781, compound

Product 1

HCID 23648642HCID 23648642, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A solution of Example 17F (340 mg, 1.00 mmol) in tetrahydrofuran (5 mL) and triethyl amine (1.0 mL) was cooled to 0° C. To this was added methyl chloroformate (200 μL, 2.59 mmol) at 0° C. The mixture was stirred at room temperature for 30 minutes. The reaction was diluted with dichloromethane, which was washed with water (1×) and concentrated. The residue was purified on silica gel eluting with hexane and ethyl acetate gradient to give the desired product as a white solid (234 mg, 59%). MS (DCI): m/z 397 (M+H); 1H NMR (300 MHz, CDCl3) δ ppm 7.65-7.77 (m, 2H), 6.94-7.07 (m, 4H), 6.85-6.93 (m, 2H), 6.40 (s, 1H), 5.01-5.16 (m, 1H), 4.44-4.58 (m, 1H), 3.71 (s, 3H), 1.58 (d, J=6.99 Hz, 3H), 1.35 (d, J=6.25 Hz, 6H).

Workup

  1. washwas washed with water (1×)
  2. concentrationconcentrated
  3. customThe residue was purified on silica gel eluting with hexane and ethyl acetate gradient

Sources & evidence

ORD record
ord-eec508340f1c4b708f8b265617d08b00
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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