Benzofuran-2-carboxylic acid → HCID 68999612, compound

HRID 1790653Notes

Reaction equation

HRID 1790653 reaction equation
CN(C)CCCN=C=NCC.[O:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH:14]=[C:13]1[C:21]([OH:23])=O.[CH3:24][O:25][C:26](=[O:53])[C@@H:27]([NH:32][C:33]([N:35]1[CH2:41][CH:40]([OH:42])[C@@H:39]([NH:43][C:44](=[O:51])[C@@H:45]([NH2:50])[CH2:46][CH:47]([CH3:49])[CH3:48])[CH2:38][CH2:37][C@H:36]1[CH3:52])=[O:34])[CH2:28][CH:29]([CH3:31])[CH3:30].C(N(C(C)C)CC)(C)C.OC1C2N=NNC=2C=CC=1>CN(C=O)C.CCOC(C)=O>[CH3:24][O:25][C:26](=[O:53])[C@@H:27]([NH:32][C:33]([N:35]1[CH2:41][C@H:40]([OH:42])[C@@H:39]([NH:43][C:44](=[O:51])[C@@H:45]([NH:50][C:21]([C:13]2[O:12][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH:14]=2)=[O:23])[CH2:46][CH:47]([CH3:48])[CH3:49])[CH2:38][CH2:37][C@H:36]1[CH3:52])=[O:34])[CH2:28][CH:29]([CH3:31])[CH3:30]

Participants

8

Reactant 5

HCID 10331Benzofuran-2-carboxylic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 69001190HCID 69001190, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 68999612HCID 68999612, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide (214 g, 1.12 mmol) was added to a solution of benzofuran-2-carboxylic acid (166 g, 1.02 mmol), (S)-2-({1-[(2R,5S)-5-((S)-2-Amino-4-methyl-pentanoylamino)-2-methyl-6-hydroxy-azepan-1-yl]-methanoyl}-amino)-4-methyl-pentanoic acid methyl ester (430 mg, 0.93 mmol), diisopropylethylamine (240 mg, 0.32 ml, 1.86 mmol), hydroxybenztriazole (151 mg, 1.12 mmol) in DMF (5 ml) and was stirred at RT overnight. The reaction mixture was stirred overnight. The reaction mixture was diluted with EtOAc (30 ml), washed with cold aq. 1N HCl, aq. sat. NaHCO3, and brine, and then dried with magnesium sulfate, filtered, concentrated in vacuo by rotary evaporation, and chromatographed (silica gel, 2% to 3% MeOH/CH2Cl2) to yield the title compound (478 mg, 84% for two steps): electrospray MS: 572.4

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. washwashed with cold aq. 1N HCl, aq. sat. NaHCO3, and brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo by rotary evaporation
  6. customchromatographed (silica gel, 2% to 3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-177873ee2f2e4660b192d6dce8351ac0
Source dataset
uspto-grants-2006_07
Patent number
US07071184B2

Reaction notes

Loading…