HCID 54046637, compound → HCID 54051289, compound

HRID 1110856Notes

Reaction equation

HRID 1110856 reaction equation
C([O:5][C:6](=[O:38])[C@H:7]([CH3:37])[NH:8][C@H:9]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:10][S:11][CH2:12][C@@H:13]([NH:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(C)(C)C>C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1>[CH2:35]([O:34][C:32]([C@@H:9]([NH:8][C@H:7]([C:6]([OH:38])=[O:5])[CH3:37])[CH2:10][S:11][CH2:12][C@@H:13]([NH:21][C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:33])[CH3:36]

Participants

4

Reactant 1

HCID 54046637HCID 54046637, compound

Product 1

HCID 54051289HCID 54051289, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

In a mixture of 50 ml of TFA and 10 ml of anisole was dissolved 20.1 g of β-isomer of N-[(R)-1-ethoxycarbonyl-2-[(S)-2-benzyloxycarbonylamino-3-phenylpropylthio]ethyl]-alanine t-butyl ester prepared in Reference Example 53. The solution was stirred at room temperature for 5 hours. The excess of the solvent was evaporated off. The residue was poured into ice water and the mixture was adjusted to a pH of 4 with a saturated aqueous solution of sodium hydrogencarbonate. Then the mixture was extracted with dichloromethane. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure. To the crystalline residue was added ether to precipitate crystals which were collected by filtration and recrystallized from dichloromethane-ether. Thus the β-isomer of the title compound was obtained. Yield 8.63 g. M.p. 124°-127° C.

Workup

  1. customprepared in Reference Example 53
  2. customThe excess of the solvent was evaporated off
  3. additionThe residue was poured into ice water
  4. extractionThen the mixture was extracted with dichloromethane
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated off under reduced pressure
  8. additionTo the crystalline residue was added ether
  9. customto precipitate crystals which
  10. filtrationwere collected by filtration
  11. customrecrystallized from dichloromethane-ether

Sources & evidence

ORD record
ord-d7c2b03225a14ae5b166e71b8bd7dea4
Source dataset
uspto-grants-1990_12
Patent number
US04977179

Reaction notes

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