Acetic Acid → HCID 20771341, compound

HRID 1814425Notes

Reaction equation

HRID 1814425 reaction equation
[OH:1][CH:2]([CH2:15][NH:16][CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][CH2:18]1)[CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].[CH2:27]([CH:32]=O)[CH2:28][C:29]([OH:31])=[O:30].CC(O)=O.[BH3-]C#N.[Na+]>CO.O>[OH:1][CH:2]([CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14])[CH2:15][N:16]([CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][CH2:18]1)[CH2:32][CH2:27][CH2:28][C:29]([OH:31])=[O:30]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 11124-Oxobutanoic acidHCID 5003444Sodium cyanoborohydrideHCID 22506221HCID 22506221, compound

Product 1

HCID 20771341HCID 20771341, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of N-[2-hydroxy-3-(1,2,3,4-tetrahydro-1-naphthylamino)propyl]phthalimide (93 mg, 0.27 mmol) in MeOH (1 ml) were added succinic semialdehyde (15 wt. % solution in water, 220 μl, 0.35 mmol), HOAc (17 μl, 0.30 mmol) and NaBH3CN (18 mg, 0.29 mmol), and the mixture was stirred at RT for 2.5 h. After adding water, the mixture was extracted with chloroform, washed with brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated under vacuum to dryness, and the residue was adsorbed on a plate of silica gel and then developed with 10% methanol/chloroform to afford 4-[[2-hydroxy-(3-phthalimido)propyl](1,2,3,4-tetrahydro-1-naphthyl)amino]butanoic acid (101 mg, 87%): MS(ES+) m/e 437 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 8.01 (br, 1H), 7.80 (m, 2H), 7.73-7.52 (m, 3H), 7.11 (t, J=7.3 Hz, 1H), 7.02 (m, 1H), 6.92-6.78 (m, 1H), 4.63 (br, 1H), 4.44-3.96 (m, 2H), 3.77-3.54 (m, 2H), 2.99-2.81 (m, 1H), 2.77-2.51 (m, 5H), 2.43 (m, 1H), 2.32 (m, 1H), 2.19-2.04 (m, 1H), 1.97 (m, 1H), 1.83 (m, 2H), 1.66 (m, 2H).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under vacuum to dryness

Sources & evidence

ORD record
ord-6377e1928eda4475a209c889a66ae1b8
Source dataset
uspto-grants-2005_04
Patent number
US06875884B1

Reaction notes

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