Dicyclohexylcarbodiimide → HCID 68602979, compound

HRID 448948Notes

Reaction equation

HRID 448948 reaction equation
[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH2:9][C:10]([OH:12])=[O:11])=[C:4]([C:13](=[O:24])[N:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])[CH3:15])[CH:3]=1.[CH3:25][Si:26]([CH3:31])([CH3:30])[CH2:27][CH2:28]O.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:25][Si:26]([CH3:31])([CH3:30])[CH2:27][CH2:28][O:11][C:10](=[O:12])[CH2:9][C:5]1[CH:6]=[C:7]([Cl:8])[C:2]([Br:1])=[CH:3][C:4]=1[C:13](=[O:24])[N:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])[CH3:15]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 180132-(Trimethylsilyl)ethanolHCID 68602961HCID 68602961, compound

Product 1

HCID 68602979HCID 68602979, compoundYield 101.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of DCM (10 mL) containing 2-{4-bromo-5-chloro-2-[(2-methoxy-phenyl)-methyl-carbamoyl]-phenyl}-acetic acid (427 mg, 1.0 mmol) and 2-trimethylsilylethanol (183 mg, 1.5 mmol), were added DMAP (18.9 mg, 0.15 mmol) and DCC (320 mg, 1.5 mmol). The mixture was stirred at rt for 24 hrs, concentrated, and then directly purified via silica gel column chromatography eluting with ethyl acetate in hexane (20%) to yield {4-bromo-5-chloro-2-[(2-methoxy-phenyl)-methyl-carbamoyl]-phenyl}-acetic acid 2-trimethylsilanyl-ethyl ester (520 mg). MS: (M-CH2CH2)+487.9/486.0; tR=3.34 min (method 1).

Workup

  1. concentrationconcentrated
  2. customdirectly purified via silica gel column chromatography
  3. washeluting with ethyl acetate in hexane (20%)

Sources & evidence

ORD record
ord-df2c2f702b99461faf6723d79fd58cd2
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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