Sodium Carbonate → (S)-2-(((Benzyloxy)carbonyl)amino)hexanedioic acid

HRID 481437Notes

Reaction equation

HRID 481437 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C@@H:13]([CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C:14]([OH:16])=[O:15].C(=O)([O-])[O-].[Na+].[Na+]>>[CH2:5]([O:4][C:2]([NH:12][C@@H:13]([CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C:14]([OH:16])=[O:15])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 92136L-2-Aminoadipic Acid

Product 1

HCID 7019809(S)-2-(((Benzyloxy)carbonyl)amino)hexanedioic acidYield 98.2%

Conditions

Temperature
5 °C

Procedure

Benzyl chloroformate (15.5 g) was added dropwise to a stirred mixture of (2S)-2-aminoadipic acid (12 g) and sodium carbonate (39.4 g) which had been cooled to 5° C. The mixture was stirred at ambient temperature for 16 hours. The mixture was washed with diethyl ether. The aqueous phase was acidified to pH1 by the addition of dilute aqueous hydrochloric acid and extracted with ethyl acetate. The organic phase was dried (MgSO4) and evaporated to give (2S)-2-benzyloxycarbonylaminoadipic acid (21.6 g).

Workup

  1. washThe mixture was washed with diethyl ether
  2. additionThe aqueous phase was acidified to pH1 by the addition of dilute aqueous hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-7698dcafa6114f829239acd9e3b72631
Source dataset
uspto-grants-1998_08
Patent number
US05789417

Reaction notes

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