Beta-Alanine → HCID 72787862, compound

HRID 2238315Notes

Reaction equation

HRID 2238315 reaction equation
O=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([CH:12]=O)[CH:5]=[CH:4][C:3]1=2.[NH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].CCN(CC)CC.[BH3-]C#N.[Na+].[CH:31]1([C:37]2[CH:45]=[CH:44][C:40]([CH2:41][O:42][NH2:43])=[CH:39][C:38]=2[C:46]([F:49])([F:48])[F:47])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>CO.CC(O)=O>[CH:31]1([C:37]2[CH:45]=[CH:44][C:40]([CH2:41][O:42][N:43]=[C:2]3[CH2:11][CH2:10][CH2:9][C:8]4[CH:7]=[C:6]([CH2:12][NH:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH:5]=[CH:4][C:3]3=4)=[CH:39][C:38]=2[C:46]([F:47])([F:48])[F:49])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1

Participants

8

Reactant 5

HCID 239Beta-AlanineHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 58200188HCID 58200188, compoundHCID 67191531O-{[4-Cyclohexyl-3-(trifluoromethyl)phenyl]methyl}hydroxylamine

Product 1

HCID 72787862HCID 72787862, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-oxo-5,6,7,8-tetrahydro-naphthalene-2-carbaldehyde (0.1 mmol) in MeOH (1 mL) is added β-alanine (0.2 mmol) and Et3N (0.16 mmol). The mixture is heated at 50° C. with stirring for 1 hour. After cooling to room temperature, NaBH3CN (0.3 mmol) is added in one portion and the resulting mixture is stirred for 30 minutes. O-(4-Cyclohexyl-3-trifluoromethyl-benzyl)-hydroxylamine (0.12 mmol) is then added to the above reaction mixture and the pH of the solution is tuned to 5-6 by adding AcOH. Purification by preparative LCMS results in 3-{[5-(4-cyclohexyl-3-trifluoromethyl-benzyloxyimino)-5,6,7,8-tetrahydro-naphthalen-2-ylmethyl]-amino}-propionic acid; 1H NMR (600 MHz, CD3OD) δ 8.00 (d, 1 H), 7.65 (s, 1 H), 7.59 (d, 1 H), 7.52 (d, 1 H), 7.35-7.26 (m, 2 H), 5.22 (s, 2 H), 4.21 (s, 2 H), 3.30 (t, 2 H), 2.94 (m, 1 H), 2.78 (m, 6 H), 1.90-1.70 (m, 7 H), 1.60-1.45 (m, 2 H), 1.45-1.30 (m, 3 H); MS (ES+): 503.2 (M+1)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringthe resulting mixture is stirred for 30 minutes
  3. customPurification by preparative LCMS
  4. customresults in 3-{[5-(4-cyclohexyl-3-trifluoromethyl-benzyloxyimino)-5,6,7,8-tetrahydro-naphthalen-2-ylmethyl]-amino}-propionic acid

Sources & evidence

ORD record
ord-c4316b3a88514c95b46d5b1544b25307
Source dataset
uspto-grants-2010_05
Patent number
US07718704B2

Reaction notes

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