L-Alaninol → (S)-Ethyl 5-(1-hydroxypropan-2-ylcarbamoyl)-4'-methylbiphenyl-3-carboxylate

HRID 1845160Notes

Reaction equation

HRID 1845160 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:19](O)=[O:20])[CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:11]=1)=[O:5])[CH3:2].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[NH2:45][C@@H:46]([CH3:49])[CH2:47][OH:48].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[OH:48][CH2:47][C@@H:46]([NH:45][C:19]([C:8]1[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[CH:9]=1)=[O:20])[CH3:49]

Participants

7

Reactant 5

HCID 80307L-AlaninolHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 581879575-(Ethoxycarbonyl)-4'-methylbiphenyl-3-carboxylic acid

Product 1

HCID 58188256(S)-Ethyl 5-(1-hydroxypropan-2-ylcarbamoyl)-4'-methylbiphenyl-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-(ethoxycarbonyl)-4′-methylbiphenyl-3-carboxylic acid (35 mg, 0.12 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (47 mg, 0.25 mmol), 1-hydroxybenzotriazole hydrate (19 mg, 0.12 mmol), and CH2Cl2 (3 mL) were added (S)-2-aminopropan-1-ol (10 mg, 0.14 mmol) and N,N-diisopropylethylamine (0.032 mL, 0.18 mmol). The mixture was stirred at room temperature overnight, and then concentrated. The residue was purified by preparative HPLC (100×21.2 mm C18 column, 30-70% MeCN/water[10 mM Et2NH]) to afford a white solid.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by preparative HPLC (100×21.2 mm C18 column, 30-70% MeCN/water[10 mM Et2NH])
  3. customto afford a white solid

Sources & evidence

ORD record
ord-70c959287c314dcfb2b4a3549cd9fb5a
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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