Phenylacetic Acid → HCID 86611434, compound

HRID 1360385Notes

Reaction equation

HRID 1360385 reaction equation
[CH3:1][CH:2]([CH3:17])[C@@H:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)[CH2:4][NH2:5].[C:18]1([CH2:24][C:25]([OH:27])=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl.C(N=C=NCCCN(C)C)C.[OH2:40].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl>[F:14][C:13]([F:16])([F:15])[C:10]([OH:26])=[O:40].[CH3:1][CH:2]([CH3:17])[C@@H:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:14])([F:15])[F:16])=[CH:9][CH:8]=1)[CH2:4][NH:5][C:25](=[O:27])[CH2:24][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 5

HCID 999Phenylacetic AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66968932HCID 66968932, compound

Product 1

HCID 86611434HCID 86611434, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2R)-3-Methyl-N2-[4-(trifluoromethyl)phenyl]butane-1,2-diamine (8 mg, 0.033 mmol) obtained in step 2, phenylacetic acid (5 mg, 0.037 mmol), 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (10 mg, 0.052 mmol), 1-hydroxybenzotriazole monohydrate (8 mg, 0.052 mmol) and triethylamine (9 μl, 0.066 mmol) were mixed in methylene chloride (3 mL), and the mixture was stirred overnight at room temperature. The solvent was evaporated and the residue was purified by purification step A to give the title compound (4.1 mg, 0.009 mmol, 26%).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by purification step A

Sources & evidence

ORD record
ord-edeb3d2d38e940bab8c687ee20c92294
Source dataset
uspto-grants-2011_02
Patent number
US07879863B2

Reaction notes

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