Hydrochloric Acid → HCID 67896332, compound

HRID 2372638Notes

Reaction equation

HRID 2372638 reaction equation
[O:1]=[C:2]([NH:11][C@H:12]([C:28]([O:30]C)=[O:29])[CH2:13][C:14]1[N:18](COCC2C=CC=CC=2)[CH:17]=[N:16][CH:15]=1)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+].Cl.O=C(N[C@H](C(O)=O)CC1N(C[O:54][CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)C=NC=1)CCC1C=CC=CC=1.[CH3:65]O>O>[O:1]=[C:2]([N:11]([CH3:65])[C@H:12]([C:28]([OH:30])=[O:29])[CH2:13][C:14]1[N:18]([O:54][CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH:17]=[N:16][CH:15]=1)[CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 53936874HCID 53936874, compoundHCID 131717209HCID 131717209, compound

Product 1

HCID 67896332HCID 67896332, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-(1-oxo-3-phenylpropyl)-3-[(phenylmethoxy)methyl]-L-histidine, methyl ester (17.2 g., 40.8 mmole) and aqueous sodium hydroxide solution (52 ml. of 1.0N solution, 52 mmole) in methanol (42 ml.) was stirred at 25° for 6 hours, after which it was diluted with water (500 ml.) and washed with ethyl acetate. The aqueous phase was neutralized by the addition of 1.0N hydrochloric acid (52 ml., 52 mmole, resulting pH of 5) and the mixture was extracted with ethyl acetate (5 times). Both the extracts and the aqueous wash were concentrated in vacuo. Each of the concentrates was stirred with hot isopropanol (500 ml. each) and filtered while hot. The filtrates were combined and partially concentrated until crystals formed. The crystals were collected and dried to give 6.5 g. of N-(1-oxo-3-phenylpropyl)-3-[(phenylmethoxy)-methyl]-L-histidine as a white powder; m.p. 163°-165°.

Workup

  1. washwashed with ethyl acetate
  2. extractionthe mixture was extracted with ethyl acetate (5 times)
  3. washBoth the extracts and the aqueous wash
  4. concentrationwere concentrated in vacuo
  5. stirringEach of the concentrates was stirred with hot isopropanol (500 ml
  6. filtrationeach) and filtered while hot
  7. concentrationpartially concentrated until crystals
  8. customformed
  9. customThe crystals were collected
  10. customdried
  11. customto give 6.5 g

Sources & evidence

ORD record
ord-b2fcb25d68bc4be4b7db65bdd90d5be0
Source dataset
uspto-grants-1992_03
Patent number
US05098924

Reaction notes

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