Hydrochloric Acid → HCID 86739454, compound

HRID 2164572Notes

Reaction equation

HRID 2164572 reaction equation
C[O:2][C:3](=[O:38])[C@H:4]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[NH:5][C:6](=[O:30])[C@H:7]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]=[CH2:28])=[C:21]([Cl:29])[CH:20]=1)[NH:8][C:9](=[O:17])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+].Cl>CC(C)=O>[CH2:26]([O:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][C@@H:7]([C:6]([NH:5][C@H:4]([C:3]([OH:38])=[O:2])[CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[O:30])[NH:8][C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:20][C:21]=1[Cl:29])[CH:27]=[CH2:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70486802HCID 70486802, compound

Product 1

HCID 86739454HCID 86739454, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

4-Allyloxy-3-chloro-phenylacetyl-(L)-phenylalanyl-(L)-phenylalanine methyl ester (5.3 g) was suspended in acetone (40 ml) to which was added aqueous sodium hydroxide (1M, 20.0 ml) and the whole was heated to effect solution. After the solution had been cooled to 0° C., the pH was adjusted to 2-3 using aqueous hydrochloric acid (3M) and the whole was extracted with ethyl acetate (80 ml). The extract was dried (anhydrous sodium sulphate) and the solvent was evaporated at reduced pressure to leave a small volume of material. Light petroleum (b.p. 80°-100° C.) was added to precipitate the solid (3.5 g) of m.p. 180°-186° C. After recrystallisation from ethyl acetate/light petroleum (b.p. 80°-100° C.), the above-named product (2.7 g), m.p. 183°-186° C., was obtained.

Workup

  1. temperaturethe whole was heated
  2. extractionthe whole was extracted with ethyl acetate (80 ml)
  3. dry with materialThe extract was dried (anhydrous sodium sulphate)
  4. customthe solvent was evaporated at reduced pressure
  5. customto leave a small volume of material
  6. customto precipitate the solid (3.5 g) of m.p. 180°-186° C
  7. customAfter recrystallisation from ethyl acetate/light petroleum (b.p. 80°-100° C.)

Sources & evidence

ORD record
ord-64d6a60fcbdc4cd8a57d5eaec0e60cda
Source dataset
uspto-grants-1985_03
Patent number
US04505898

Reaction notes

Loading…