Isobutylamine → HCID 58187986, compound

HRID 1845154Notes

Reaction equation

HRID 1845154 reaction equation
O[CH2:2][C@@H:3]([NH:5][C:6]([C:8]1[CH:9]=[C:10]([C:21]([OH:23])=O)[CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:13]=1)=[O:7])[CH3:4].Cl.CN(C)CCCN=C=NCC.[OH2:36].ON1C2C=CC=CC=2N=N1.[CH3:47][CH:48]([CH3:51])[CH2:49][NH2:50].C(N(CC)C(C)C)(C)C>CCOC(C)=O.CN(C=O)C.C(Cl)Cl>[OH:36][CH2:4][C@@H:3]([NH:5][C:6]([C:8]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:11]=[C:10]([C:21]([NH:50][CH2:49][CH:48]([CH3:51])[CH3:47])=[O:23])[CH:9]=1)=[O:7])[CH3:2]

Participants

9

Reactant 5

HCID 6558IsobutylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 58188124HCID 58188124, compound

Product 1

HCID 58187986HCID 58187986, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (S)-5-(1-hydroxypropan-2-ylcarbamoyl)-4′-methylbiphenyl-3-carboxylic acid (25 mg, 0.080 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (30 mg, 0.16 mmol), 1-hydroxybenzotriazole hydrate (12 mg, 0.080 mmol), CH2Cl2 (3 mL), and DMF (0.5 mL) were added 2-methyl-1-propanamine (12 mg, 0.16 mmol) and N,N-diisopropylethylamine (0.021 mL, 0.12 mmol). The mixture was stirred at room temperature overnight, and then diluted with EtOAc, washed with aq. NaHCO3, brine, dried (Na2SO4), and 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 foam.

Workup

  1. washwashed with aq. NaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC (100×21.2 mm C18 column, 30-70% MeCN/water[10 mM Et2NH])
  5. customto afford a white foam

Sources & evidence

ORD record
ord-9e75d18fd55942b7a475149021b22134
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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