Triethylamine → HCID 69871072, compound

HRID 2417121Notes

Reaction equation

HRID 2417121 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH:5]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])([CH3:18])[CH3:17])=[CH:11][CH:10]=1)[CH3:2].C(N(CC)CC)C.[C:40]1([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:45]=[CH:44][C:43]([C:46](Cl)=[O:47])=[CH:42][CH:41]=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:32])[CH:5]([N:24]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:46]([C:43]1[CH:44]=[CH:45][C:40]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[CH:41][CH:42]=1)=[O:47])[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])([CH3:18])[CH3:17])=[CH:11][CH:10]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 841514-Phenylbenzoyl chlorideHCID 10972287HCID 10972287, compound

Product 1

HCID 69871072HCID 69871072, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A sample of 2-benzylamino-4-[4-(1-ethoxycarbonyl-1-methyl-ethoxy)-phenoxy]-butyric acid ethyl ester (490 mg, 1.10 mmol) was dissolved in 10 mL of methylene chloride followed by addition of triethylamine (0.31 mL, 2.21 mmol) and biphenyl-4-carbonyl chloride (287 mg, 1.33 mmol). The reaction was allowed to stir at room temperature for 12 hours then partitioned between additional methylene chloride (50 mL) and 0.1 N HCl (50 mL). The organic phase was dried over sodium chloride, then concentrated under reduced pressure to yield 687 mg (100%) of an oil. HPLC RT1=7.65 min; 1H NMR (400 MHz, CDCl3) δ 7.60-7.20 (m, 14H), 6.77-6.46 (m, 4H), 4.91-4.45 (m, 2H), 4.19-3.66 (m, 7H), 2.78-2.12 (m, 2H), 1.49 (s, 6H), 1.25-1.22 (m, 6H).

Workup

  1. customthen partitioned between additional methylene chloride (50 mL) and 0.1 N HCl (50 mL)
  2. dry with materialThe organic phase was dried over sodium chloride
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0a9b871fe4e94fb6ae693484cc82ae5d
Source dataset
uspto-grants-2004_11
Patent number
US06825222B2

Reaction notes

Loading…