L-Alaninol → HCID 58188282, compound

HRID 1845152Notes

Reaction equation

HRID 1845152 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:18]([OH:20])=O)[CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[CH:10]=1)=[O:4].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>CCOC(C)=O.C(Cl)Cl>[OH:47][CH2:46][C@@H:45]([NH:44][C:18]([C:7]1[CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:10]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[CH:8]=1)=[O:20])[CH3:48]

Participants

8

Reactant 5

HCID 80307L-AlaninolHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 58188126HCID 58188126, compound

Product 1

HCID 58188282HCID 58188282, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-(methoxycarbonyl)-4′-methylbiphenyl-3-carboxylic acid (0.60 g, 2.2 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (470 mg, 2.4 mmol), 1-hydroxybenzotriazole hydrate (340 mg, 2.2 mmol), and CH2Cl2 (5 mL) were added (S)-2-aminopropan-1-ol (180 mg, 2.4 mmol) and N,N-diisopropylethylamine (0.58 mL, 3.3 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 silica gel column (0-80% EtOAc/hexane) to yield a white solid. LC-MS: 328.2 [M+1]+; 1H NMR (400 MHz, DMSO-d6): δ 8.48 (d, 1H, J=8.0 Hz), 8.40 (t, 1H, J=1.6 Hz), 8.37 (t, 1H, J=1.6 Hz), 8.28 (t, 1H, J=1.6 Hz), 7.69 (d, 2H, J=8.0 Hz), 7.34 (d, 2H, J=8.0 Hz), 4.78 (t, 1H, J=5.6 Hz), 4.07 (m, 1H), 3.92 (s, 3H), 3.49 (m, 1H), 3.38 (m, 1H), 2.37 (s, 3H), 1.16 (d, 3H, J=6.8 Hz).

Workup

  1. washwashed with aq. NaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column (0-80% EtOAc/hexane)
  5. customto yield a white solid

Sources & evidence

ORD record
ord-4c4f5f0e8739468d9ce9d0159f55fcbd
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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