Acetyl chloride → (2'-Acetoxymethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

HRID 38704Notes

Reaction equation

HRID 38704 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23]NCC(=O)N)[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.C[O:31][C:32](=[O:54])[CH2:33]C1C=C(C2C=CC(C(F)(F)F)=CC=2CO)C(OC)=CC=1.C(N(CC)CC)C.C(Cl)(=O)C>C(Cl)Cl.O>[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:15][C:14]=2[CH2:23][O:54][C:32](=[O:31])[CH3:33])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 66606415(2'-Hydroxymethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl esterHCID 66634341{2'-[(Carbamoylmethyl-amino)-methyl]-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl}-acetic acid methyl ester

Product 1

HCID 67429487(2'-Acetoxymethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of {2′-[(carbamoylmethyl-amino)-methyl]-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl}-acetic acid methyl ester and (2′-hydroxymethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester (0.223 g, 0.54 mmol) in CH2Cl2 (2.2 mL) was added triethylamine (0.11 mL, 0.82 mmol), followed by acetyl chloride (0.06 mL, 0.82 mmol), and the reaction was stirred at room temperature for 45 minutes. The mixture was worked up with CH2Cl2 and H2O, and the crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes, then 5% MeOH in CH2Cl2) to give the title compound.

Workup

  1. customthe crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-4de992f87b3646f09ad1aef0301ebf0f
Source dataset
uspto-grants-2013_09
Patent number
US08524748B2

Reaction notes

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