Hydrochloric Acid → HCID 69629149, compound

HRID 891253Notes

Reaction equation

HRID 891253 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([O:20][CH2:21][CH3:22])[C:17]([OH:19])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:24][C@H:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:26][OH:27].OS(O)(=O)=O.[OH-].[Na+]>CN(C1C=CN=CC=1)C.CCOC(C)=O.C(Cl)CCl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]([O:20][CH2:21][CH3:22])[C:17]([NH:24][C@H:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:26][OH:27])=[O:19])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric Acid2×HCID 14798Sodium HydroxideHCID 2724025(R)-beta-aminophenethyl alcoholHCID 109245703-[4-(Benzyloxy)phenyl]-2-ethoxypropanoic acid

Product 1

HCID 69629149HCID 69629149, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

3-[4-(Benzyloxy)phenyl]-2-ethoxypropanoic acid (30.6 kg, 88 mol) and DMAP (12.9 kg) were dissolved in CH2CI2 (192 L) and cooled to 0° C. To the clear solution EDC×HCl (20.2 kg) was added in 10 minutes. In 18 minutes a solution of (2R)-2-amino-2-phenyl-1-ethanol (14.5 kg, 105.6 mol) in CH2CI2 (60 L) was added, keeping the temperature below 2° C. The reaction mixture was kept at 0° C. for 2 hours and then heated to reflux for ca. 3 hours. The solvent was then distilled off (110 L). EtOAc (110 L) was added and the temperature lowered to 10° C. Over 30 min 1M H2SO4 (110 L, 110 mol) was added, the phases separated and the organic phase extracted with H2SO4 (110 L, 110 mol). To the combined organic phases, 110 L EtOAc and 1 M NaOH (110 L, 110 mol) were added at 10° C. (pH 10). The phases were separated and the organic phase washed with saturated NaCl solution.

Workup

  1. customthe temperature below 2° C
  2. temperatureheated
  3. temperatureto reflux for ca. 3 hours
  4. distillationThe solvent was then distilled off (110 L)
  5. additionEtOAc (110 L) was added
  6. customlowered to 10° C
  7. customthe phases separated
  8. customThe phases were separated
  9. washthe organic phase washed with saturated NaCl solution

Sources & evidence

ORD record
ord-8c7920cfc19744228735cdd9ae9b8fb0
Source dataset
uspto-grants-2006_02
Patent number
US07002037B2

Reaction notes

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