HCID 54215249, compound → HCID 21153507, compound

HRID 1413126Notes

Reaction equation

HRID 1413126 reaction equation
C([O:5][C:6](=[O:33])[C@H:7]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[NH:8][C:9](=[O:25])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:24])[CH:16]([CH3:23])[CH2:17][S:18][C:19](=[O:22])[CH2:20][CH3:21])(C)(C)C>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[C:19]([S:18][CH2:17][CH:16]([CH3:23])[C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C:9]([NH:8][C@H:7]([C:6]([OH:33])=[O:5])[CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:25])=[O:24])(=[O:22])[CH2:20][CH3:21]

Participants

4

Reactant 1

HCID 54215249HCID 54215249, compound

Product 1

HCID 21153507HCID 21153507, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

The 1-(3-propanoylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine tert-butyl ester obtained was dissolved in a mixture of anisole (10 ml) and trifluoroacetic acid (20 ml). The solution was allowed to stand at room temperature for one hour and concentrated to dryness under reduced pressure. The residue was chromatographed on silica gel with chloroform-methanol (98:2) to give 1-(3-propanoylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine. The diastereomeric mixture thus obtained was dissolved in a proper amount of diethyl ether. The solution was seeded with crystals of the title compound and stored in a refrigerator. The precipitated crystals were collected and recrystallized repeatedly from diethyl ether/petroleum ether to give the title compound, m.p. 107°-114° C. [α]D20 =-81.1° (c=1.00, ethanol)

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. customThe residue was chromatographed on silica gel with chloroform-methanol (98:2)

Sources & evidence

ORD record
ord-9a0bfd5994e140ad96aa5e89b5d9545f
Source dataset
uspto-grants-1981_02
Patent number
US04248883

Reaction notes

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