Hydrochloric Acid → 4-[(3-Benzyloxy-4-methoxybenzoyl)amino]-3-hydroxy-butyric acid

HRID 1462943Notes

Reaction equation

HRID 1462943 reaction equation
[NH2:1][CH2:2][CH:3]([OH:8])[CH2:4][C:5]([OH:7])=[O:6].[C:9]([O:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[C:21](Cl)=[O:22])(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O1CCCC1.Cl>[OH-].[Na+]>[CH2:9]([O:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[C:21]([NH:1][CH2:2][CH:3]([OH:8])[CH2:4][C:5]([OH:7])=[O:6])=[O:22])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21494-Amino-3-hydroxybutanoic acidHCID 8028TetrahydrofuranHCID 211878683-Benzoyloxy-4-methoxybenzoylchloride

Product 1

HCID 204524084-[(3-Benzyloxy-4-methoxybenzoyl)amino]-3-hydroxy-butyric acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

18.1 g of 4-amino-3-hydroxy-butyric acid are dissolved in 176 ml of 2 N sodium hydroxide. To this there are added within 2 minutes 14.0 g of 3-benzoyloxy-4-methoxybenzoylchloride and subsequently 30 ml of tetrahydrofuran. The mixture is stirred intensively at room temperature for 2 hours, then treated with ice and acidified with concentrated hydrochloric acid. The separated solid is filtered off and washed with water. After drying, the filter cake is boiled in ethyl acetate and the insoluble portion is recrystallised from tetrahydrofuran/n-hexane (3.6:1). There is obtained 4-[(3-benzyloxy-4-methoxybenzoyl)amino]-3-hydroxy-butyric acid of melting point 158°-160° C.

Workup

  1. additiontreated with ice
  2. filtrationThe separated solid is filtered off
  3. washwashed with water
  4. customAfter drying
  5. customthe insoluble portion is recrystallised from tetrahydrofuran/n-hexane (3.6:1)

Sources & evidence

ORD record
ord-e78da048b7de406085609d7a5281fa51
Source dataset
uspto-grants-1984_07
Patent number
US04461906

Reaction notes

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