Trifluoroacetic acid → HCID 69519547, compound

HRID 1831423Notes

Reaction equation

HRID 1831423 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:8][C:7](=[O:9])[O:6][C:4](=O)[CH2:3]1.C(N(C(C)C)CC)(C)C.[NH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30](=[O:39])[N:31]([CH3:38])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:25][CH:24]=1.C(O)(C(F)(F)F)=O.S(Cl)(Cl)=O>C(Cl)Cl.C(O)C>[CH3:10][C:2]1([CH3:1])[CH2:3][C:4](=[O:6])[N:20]([CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][C:30](=[O:39])[N:31]([CH3:38])[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[CH:27][CH:28]=2)[C:7](=[O:9])[CH2:8]1

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 24386Thionyl ChlorideHCID 778133,3-Dimethylglutaric anhydrideHCID 81531DiisopropylethylamineHCID 69520583Methyl-phenyl-carbamic acid 4-(2-amino-ethyl)phenyl Ester

Product 1

HCID 69519547HCID 69519547, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3,3-dimethylglutaric anhydride (0.3 mmol), diisopropylethylamine (0.30 mmol) and N-methyl-N-phenyl-carbamic acid 4-(2-amino-ethyl)phenyl ester as its TFA salt (0.3 mmol) in CH2Cl2 (3 mL) was stirred 1 h at rt. Thionylchloride (3 mmol) was added and the mixture was stirred for 2 h at rt. Addition of ethanol (5 mL) followed by evaporation to dryness gave a crude product which was purified by flash chromatography (Quad flash 12, EtOAc-heptane 1:1). This gave the title compound in 23% yield as crystals. Furthermore 3,3-dimethyl-4-{2-[4-(methyl-phenyl-carbamoyloxy)-phenyl]-ethylcarbamoyl}-butyric acid ethyl ester could be isolated in 27% yield as an oil (see characterization below)

Workup

  1. customfollowed by evaporation to dryness
  2. customgave a crude product which
  3. customwas purified by flash chromatography (Quad flash 12, EtOAc-heptane 1:1)

Sources & evidence

ORD record
ord-cfa39811ff03414483cd0c7f2373d286
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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