HCID 14233365, compound → HCID 14233368, compound

HRID 34685Notes

Reaction equation

HRID 34685 reaction equation
C([NH:4][C@@H:5]([C:21]([OH:23])=[O:22])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=1)(=O)C>Cl>[C:13]([C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[CH2:6][C@H:5]([C:21]([OH:23])=[O:22])[NH2:4])(=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 1

HCID 14233365HCID 14233365, compound

Product 1

HCID 14233368HCID 14233368, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 2.0 g of N-Acetyl-m-benzoyl-D-phenylalanine in 15 ml of 8N hydrochloric acid was heated to 100° in the steam bath for 4 h. The suspension was filtered hot, solid was washed with 8N hydrochloric acid, then water. The filtrate was neutralized with 1N sodium hydroxide and yielded 1.503 g of m-benzoyl-D-phenylalanine after water washing and drying under nitrogen, m.p. 230°-231°, [α]D25 =+3.3±0.8 C=0.90 g/100 ml 1N HCl. Anal.: Calcd. for C16H15NO3 : C, 71.36; H, 5.61; N, 5.20. Found: C, 70.43; H, 5.34; N, 5.37.

Workup

  1. temperaturewas heated to 100° in the steam bath for 4 h
  2. filtrationThe suspension was filtered hot
  3. washsolid was washed with 8N hydrochloric acid

Sources & evidence

ORD record
ord-3f848cf4f5904c948f0deabc712f2621
Source dataset
uspto-grants-1988_08
Patent number
US04762881

Reaction notes

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