Benzofuran-2-carboxylic acid → HCID 68999612, compound

HRID 229837Notes

Reaction equation

HRID 229837 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-c5be68bfaee841819e03f549a7faeedd
Source dataset
uspto-grants-2009_07
Patent number
US07563784B2

Reaction notes

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