HCID 131712164, compound → HCID 131712166, compound

HRID 894351Notes

Reaction equation

HRID 894351 reaction equation
C[O:2][C:3](=[O:41])[C@H:4]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[NH:5][C:6](=[O:33])[C:7](=[CH: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:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>CO>[C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C:9]([NH:8][C:7]([C:6]([NH:5][C@H:4]([C:3]([OH:41])=[O:2])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:33])=[CH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:25])([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]

Participants

3

Reactant 1

HCID 131712164HCID 131712164, compound

Product 1

HCID 131712166HCID 131712166, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

There was added 2 ml of N-sodium hydroxide to a solution of 0.556 g (0.001 mole) of N-carbobenzoxy-L-prolyl-dehydrophenylalanyl-L-phenylalanine methyl ester in 10 ml of methanol. The mixture was stirred at room temperature for 2 hours and concentrated in vacuo. The residual aqueous solution was washed with ethyl acetate and after acidification with 4 N-hydrochloric acid, the resulting separated oil was extracted into ethyl acetate and the extracts were dried over anhydrous Na2SO4. The solvent was evaporated in vacuo and the residual oil was purified on a column of silica gel (60-200 mesh) by elution with ether. The oily product was crystallized from ether to yield 0.357 g (66%) of N-carbobenzoxy-L-prolyl-dehydrophenylalanyl-L-phenylalanine, mp 171°-173°, RfA 0.68, [α]D26 =-30.2° (c, 1% in THF); ir (CHCl3) 1730 (Sh, C=O9, 1670 (C=O), 1630 cm-1 (Sh, C=C); NMR (CDCl3) δ1.5-2.3 (m, 4 H, Pro ring), 3.0-3.5 (m, 2H, >CH--CH2Ph), 3.2-3.7 (m, 2H, Pro ring), 4.2-4.5 (m, 1H>CHCH2Ph), 4.6-5.0 (m, 1H, Pro ring), 5.0 (s, 2H,>N-OCOCH2Ph), 7.0-7.6 (m, 16H, ArH and PhCH=C--), 8.0-8.27 (br, 1H, -NH exchanged by D2O); 9.03-9.5 (br, 2H, -NH or -COOH, exchanged by D2O).

Workup

  1. concentrationconcentrated in vacuo
  2. washThe residual aqueous solution was washed with ethyl acetate
  3. customafter acidification with 4 N-hydrochloric acid, the resulting separated oil
  4. extractionwas extracted into ethyl acetate
  5. dry with materialthe extracts were dried over anhydrous Na2SO4
  6. customThe solvent was evaporated in vacuo
  7. customthe residual oil was purified on a column of silica gel (60-200 mesh) by elution with ether
  8. customThe oily product was crystallized from ether

Sources & evidence

ORD record
ord-faefaed6559f441fb78b99a571102d47
Source dataset
uspto-grants-1981_08
Patent number
US04283328

Reaction notes

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