L-Alaninol → (S)-N-(1-Hydroxypropan-2-yl)-4'-methyl-5-(methylsulfonyl)biphenyl-3-carboxamide

HRID 1845159Notes

Reaction equation

HRID 1845159 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:11]=[C:10]([C:18](O)=[O:19])[CH:9]=2)=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[NH2:44][C@@H:45]([CH3:48])[CH2:46][OH:47].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[OH:47][CH2:46][C@@H:45]([NH:44][C:18]([C:10]1[CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[CH:13]=[C:12]([S:14]([CH3:17])(=[O:15])=[O:16])[CH:11]=1)=[O:19])[CH3:48]

Participants

7

Reactant 5

HCID 80307L-AlaninolHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 581879934'-Methyl-5-(methylsulfonyl)biphenyl-3-carboxylic acid

Product 1

HCID 58188317(S)-N-(1-Hydroxypropan-2-yl)-4'-methyl-5-(methylsulfonyl)biphenyl-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4′-methyl-5-(methylsulfonyl)biphenyl-3-carboxylic acid (50 mg, 0.17 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (36 mg, 0.19 mmol), 1-hydroxybenzotriazole hydrate (26 mg, 0.17 mmol), and CH2Cl2 (2 mL) were added (S)-2-aminopropan-1-ol (19 mg, 0.26 mmol) and N,N-diisopropylethylamine (0.045 mL, 0.26 mmol). The mixture was stirred at room temperature overnight and then concentrated in vacuo. The residue was purified by preparative HPLC (100×20.2 mm, C18 column; 30-60% MeCN-water[10 mM Et2NH]) to yield a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by preparative HPLC (100×20.2 mm, C18 column; 30-60% MeCN-water[10 mM Et2NH])
  3. customto yield a white solid

Sources & evidence

ORD record
ord-8862f8888778490287097cd05fc0766c
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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