Hydrochloric Acid → 4-[(1S)-1-[[(Benzyloxy)carbonyl]amino]ethyl]benzoic acid

HRID 1293178Notes

Reaction equation

HRID 1293178 reaction equation
[NH2:1][C@H:2]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)[CH3:3].Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].Cl>[OH-].[Na+]>[CH2:17]([O:16][C:14]([NH:1][C@H:2]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)[CH3:3])=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 28286491(S)-4-(1-Aminoethyl)benzoic acid

Product 1

HCID 575722614-[(1S)-1-[[(Benzyloxy)carbonyl]amino]ethyl]benzoic acidYield 88.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a cooled (0° C.) mixture of 4-[(1S)-1-aminoethyl]benzoic acid (Chem. Eur. J. 1999, 5, 1095, 16.2 g, 98 mmol) and 2 N sodium hydroxide aqueous solution (100 mL) was added benzyl chloroformate (20.5 g, 120 mmol) dropwise over 30 min period followed by the addition of additional 2 N sodium hydroxide aqueous solution (70 mL). The reaction mixture was stirred overnight at room temperature and then acidified to pH 1 with concentrated hydrochloric acid. The resulting precipitate was filtered, washed with water (100 mL), and then vacuum dried to yield 26 g (88%) of the title compounds as white solids: 1H-NMR (CDCl3) δ 7.95 (2H, d, J=8.1 Hz), 7.40–7.15 (7H, m), 5.12–4.94 (3H, m), 4.82 (1H, br.s), 1.40 (3H, d, J=7.0 Hz); MS (ESI) m/z 300 (M+H)+, 298 (M−H)−.

Workup

  1. temperatureTo a cooled
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water (100 mL)
  4. customvacuum dried

Sources & evidence

ORD record
ord-02635fbf260f4d25a7bac8187c71bb0e
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

Loading…