Hydrochloric Acid → D-Aspartic acid, N-(phenylmethyl)-3-((phenylmethyl)amino)-, (3S)-rel-

HRID 976019Notes

Reaction equation

HRID 976019 reaction equation
[C@H:1](Br)([C:7]([OH:9])=[O:8])[C@H:2](Br)[C:3]([OH:5])=[O:4].[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>>[CH2:11]([NH:18][CH:2]([CH:1]([NH:18][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7]([OH:9])=[O:8])[C:3]([OH:5])=[O:4])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 6416112,3-Dibromosuccinic acid, meso-

Product 1

HCID 108349D-Aspartic acid, N-(phenylmethyl)-3-((phenylmethyl)amino)-, (3S)-rel-

Conditions

Temperature
50 °C

Procedure

To a mechanically stirred solution of meso-2,3-dibromosuccinic acid (27.6 g, 0.100 mol) in alcohol (200 ml) was slowly added benzylamine (85 g, 0.80 mol) at ambient temperature. After complete addition the mixture was refluxed overnight. A heavy precipitate of salts appeared. The mixture was cooled to 50° C. and concentrated hydrochloric acid was added until pH was 4-5. The precipitate was filtered off, washed several times with water and alcohol and dried.

Workup

  1. customat ambient temperature
  2. additionAfter complete addition the mixture
  3. temperaturewas refluxed overnight
  4. filtrationThe precipitate was filtered off
  5. washwashed several times with water and alcohol
  6. customdried

Sources & evidence

ORD record
ord-6aeed64457d44dbab7339ed680c6b5a5
Source dataset
uspto-grants-1997_03
Patent number
US05610141

Reaction notes

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