Beta-Alanine → HCID 11316614, compound

HRID 2353358Notes

Reaction equation

HRID 2353358 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[C:7]([N:9]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH:18]=O)[CH:15]=3)[CH2:10]2)[CH:6]=[CH:5][C:4]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[NH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32].CCN(CC)CC.[BH4-].[Na+]>CO>[F:26][C:2]([F:1])([F:27])[C:3]1[CH:8]=[C:7]([N:9]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH2:18][NH:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[CH:15]=3)[CH2:10]2)[CH:6]=[CH:5][C:4]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 86596037HCID 86596037, compound

Product 1

HCID 11316614HCID 11316614, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(2-trifluoromethyl-biphenyl-4-yl)-2,3-dihydro-1H-isoindole-5-carbaldehyde (19 mg, 0.05 mmol) in 3 mL MeOH, β-alanine (8.7 mg, 0.1 mmol) and catalytic amount Et3N are added. The suspension is heated to 50° C. for 0.5 hours, followed by adding 2 mg of NaBH4. After pre-LC-MS, 8 mg of 3-{[2-(2-trifluoromethyl-biphenyl-4-yl)-2,3-dihydro-1H-isoindol-5-ylmethyl]-amino}-propionic acid is obtained as a white solid. MS m/z 441[M+1]+. 1H NMR (DMSO-d6): δ 7.08-7.26 (m, 9H), 6.80 (brs, 2H), 4.53 (s, 4H), 3.68 (s, 2H), 2.62 (t, 2H), 2.16 (t, 2H).

Sources & evidence

ORD record
ord-b169d833da894b91805f1d3f6ed9dc05
Source dataset
uspto-grants-2010_07
Patent number
US07750021B2

Reaction notes

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