Dicyclohexylcarbodiimide → HCID 68602979, compound

HRID 661700Notes

Reaction equation

HRID 661700 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-9fbfef44ba5d4bf4836a2a1db839b103
Source dataset
uspto-grants-2011_12
Patent number
US08084614B2

Reaction notes

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