Trifluoroacetic acid → HCID 178511828, compound

HRID 1272370Notes

Reaction equation

HRID 1272370 reaction equation
CC(C)(OC([NH:7][C@H:8]([CH2:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[F:21])[CH2:9][C:10]([OH:12])=O)=O)C.[CH2:23]([N:25]=[C:26]=[N:27][CH2:28][CH2:29][CH2:30]N(C)C)[CH3:24].[OH:34]C1C2N=NNC=2C=CC=1.C([N:47]([CH:50](C)C)CC)(C)C.[F:53][C:54]([F:59])([F:58])C(O)=O>ClCCl>[NH2:7][C@H:8]([CH2:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[F:21])[CH2:9][C:10]([N:47]1[CH2:50][CH2:30][C:29]2[C:28]([OH:34])=[N:27][C:26]([C:54]([F:59])([F:58])[F:53])=[N:25][C:23]=2[CH2:24]1)=[O:12]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 11347588(R)-b-(Boc-amino)-2,5-difluorobenzenebutanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 178511828HCID 178511828, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 30 mg (0.10 mmol) of (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]4-(2,5-difluorophenyl)butanoic acid, 34 mg (0.12 mmol) of amine from Step B, 25 mg (0.12 mmol) of ethyl dimethylaminopropylcarbodiimide (EDC), and 18 mg (0.12 mmol) of hydroxybenzotriazole (HOBt) in 1.0 mL of dichloromethane was treated with 0.050 mL of diisopropylethylamine. The reaction mixture was sonicated for 5 min, then shaken for 3 days at ambient temperature. The mixture was diluted with 1 mL of dichloromethane, treated with 2 mL of trifluoroacetic acid (TFA), and concentrated in vacuo. Purification by HPLC (YMC C18 Pro column, gradient elution, 10–90% MeCN:H2O containing 0.1% TFA) gave 40 mg of a viscous gum which was converted to free base on a 1-g SCX column to provide 25 mg of a white solid. The solid was triturated with ether, collected and dried under vacuo to give 21.2 mg of the title compound as a white powder. LC-MS 417.1 (M+1).

Workup

  1. customThe reaction mixture was sonicated for 5 min
  2. concentrationconcentrated in vacuo
  3. customPurification
  4. washby HPLC (YMC C18 Pro column, gradient elution, 10–90% MeCN:H2O containing 0.1% TFA)

Sources & evidence

ORD record
ord-7b9bddbb5701424c853384f45e6e4771
Source dataset
uspto-grants-2007_04
Patent number
US07208498B2

Reaction notes

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