HCID 16107461, compound → HCID 16107462, compound

HRID 556216Notes

Reaction equation

HRID 556216 reaction equation
[N:1]([CH2:4][C:5]([CH2:24][O:25][C:26]([C:35]([F:38])([F:37])[F:36])([C:31]([F:34])([F:33])[F:32])[C:27]([F:30])([F:29])[F:28])([CH2:9][O:10][C:11]([C:20]([F:23])([F:22])[F:21])([C:16]([F:19])([F:18])[F:17])[C:12]([F:15])([F:14])[F:13])[C:6]([OH:8])=[O:7])=[N+]=[N-]>[Pd].CO>[NH2:1][CH2:4][C:5]([CH2:9][O:10][C:11]([C:12]([F:13])([F:14])[F:15])([C:20]([F:21])([F:22])[F:23])[C:16]([F:17])([F:18])[F:19])([CH2:24][O:25][C:26]([C:27]([F:29])([F:28])[F:30])([C:31]([F:34])([F:33])[F:32])[C:35]([F:38])([F:37])[F:36])[C:6]([OH:8])=[O:7]

Participants

4

Reactant 1

HCID 16107461HCID 16107461, compound

Product 1

HCID 16107462HCID 16107462, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of Palladium on carbon (2.5 g) in methanol (200 mL) was degassed for 2 minutes and stirred under a hydrogen atmosphere for 30 minutes. A solution of acid 12 (10.7 g, 17.5 mmol) in methanol (10 mL) was then added and the resulting mixture was stirred at room temperature under a hydrogen atmosphere for additional 30 hours. After removal solvent, the resulting residue was purified by flash column chromatography on silica gel (methanol/dichloromethane=10/1) to give the amino acid 1 as a solid (10.1 g, 98%). mp. 182-184° C.; 1H NMR (400 MHz, CD3OD) δ 2.99 (s, 2H), 4.22 (d, J=9.2 Hz, 2H), 4.49 (d, J=8.4 Hz, 2H); 19F NMR (376 MHz, CD3OD) δ −71.00 (s); 13C NMR (100.7 MHz, CD3OD) δ 41.7, 52.1, 69.9, 80.9 (m), 121.7 (q, J=292.6 Hz), 175.0; MS (CI) m/z 586 (M++1, 100); HRMS (CI) Calcd for C13H10F18NO4: 586.0322, Found: 586.0285.

Workup

  1. customwas degassed for 2 minutes
  2. stirringthe resulting mixture was stirred at room temperature under a hydrogen atmosphere for additional 30 hours
  3. customAfter removal solvent
  4. customthe resulting residue was purified by flash column chromatography on silica gel (methanol/dichloromethane=10/1)

Sources & evidence

ORD record
ord-65b3560d902e43149c5ceb7a98f7f83f
Source dataset
uspto-grants-2011_11
Patent number
US08052961B2

Reaction notes

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