Acetic Acid → HCID 69529871, compound

HRID 1814432Notes

Reaction equation

HRID 1814432 reaction equation
[CH:1]1([NH:11][CH2:12][CH2:13][CH2:14][N:15]2[C:19](=[O:20])[C:18]3=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]3[C:16]2=[O:25])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH2:26]([CH:31]=O)[CH2:27][C:28]([OH:30])=[O:29].CC(O)=O.[BH3-]C#N.[Na+]>CO.O>[C:19]1(=[O:20])[N:15]([CH2:14][CH2:13][CH2:12][N:11]([CH:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)[CH2:31][CH2:26][CH2:27][C:28]([OH:30])=[O:29])[C:16](=[O:25])[C:17]2=[CH:24][CH:23]=[CH:22][CH:21]=[C:18]12

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 11124-Oxobutanoic acidHCID 5003444Sodium cyanoborohydrideHCID 22506225HCID 22506225, compound

Product 1

HCID 69529871HCID 69529871, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of N-[3-(1,2,3,4-tetrahydro-1-naphthylamino)propyl]phthalimide (200 mg, 0.60 mmol) in MeOH (10 ml) were added succinic semialdehyde (15 wt. % solution in water, 0.45 ml, 0.72 mmol), HOAc (41 μl, 0.72 mmol) and NaBH3CN (45 mg, 0.72 mmol), and the mixture was stirred at RT for 2.5 h. After adding water, the mixture was extracted with chloroform, washed with water and brine, dried over sodium sulfate, and filtered. The filtrate was concentrated under vacuum to dryness, and the residue was chromatographed on silica gel (eluting with 5% methanol/chloroform) to afford 4-[[(3-phthalimido)propyl](1,2,3,4-tetrahydro-1-naphthyl)amino]butanoic acid (207 mg, 82%): MS(ES+) m/e 421 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 7.83 (dd, J=5.6, 2.9 Hz, 2H), 7.72 (m, 2H), 7.65 (d, J=7.6 Hz, 1H), 7.15 (m, 1H), 7.08 (m, 1H), 7.00 (d, J=7.3 Hz, 1H), 4.28 (m, 1H) 3.75 (m, 1H), 3.65 (m, 1H), 2.80-2.55 (m, 6H), 2.47 (m, 1H), 2.30 (m, 1H), 2.06-1.86 (m, 5H), 1.74-1.66 (m, 3H).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under vacuum to dryness
  6. customthe residue was chromatographed on silica gel (eluting with 5% methanol/chloroform)

Sources & evidence

ORD record
ord-a8783a85aa364c6094ebc041541821fb
Source dataset
uspto-grants-2005_04
Patent number
US06875884B1

Reaction notes

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