Pyridine → HCID 22847765, compound

HRID 1655754Notes

Reaction equation

HRID 1655754 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:20](Cl)(=O)[C:21](Cl)=O.C([C@:33](O)([CH2:37][C:38](=[O:40])[NH2:39])[C:34](O)=[O:35])C1C=CC=CC=1.[N:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>>[CH2:47]([NH:42][C:34](=[O:35])[C@@H:33]([O:18][C:17](=[O:19])[C@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:37][C:38]([NH2:39])=[O:40])[C:46]1[CH:21]=[CH:20][CH:43]=[CH:44][CH:45]=1

Participants

5

Reactant 4

HCID 1049Pyridine2×HCID 65578Oxalyl chlorideHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 54012219HCID 54012219, compound

Product 1

HCID 22847765HCID 22847765, compound

Procedure

0.8 g of t-butoxycarbonyl-L-phenylalanine was dissolved in 5 ml of pyridine, treated at -5° with 0.3 ml of oxalyl chloride and stirred at 0-5° for 10 minutes. After the addition of 0.7 g of benzyl-(S)-3-carbamoyl-2-hydroxypropionic acid (which was prepared according to the directions in Agr. Biol. Chem. 40, 1651 (1976) and Int. J. Peptide Protein Res. 20, 35 (1982)) in 1 ml of pyridine, the mixture was stirred at 0°-5° for 2 hours and thereafter at room temperature for 1 hour. The reaction mixture was then poured onto ice and extracted twice with 50 ml of ethyl acetate each time. The combined organic extracts were washed with 50 ml of 3N hydrochloric acid and 50 ml of saturated sodium bicarbonate solution, dried over sodium sulfate and evaporated. The residue was purified by flash chromatography on 50 g of silica gel using a 10:1 mixture of methylene chloride and methanol as the eluting agent to obtain there was obtained 0.9 g of (S)-2-[[N-(t-butoxycarbonyl)-3-phenyl-L-alanyl]oxy]succinamide benzyl ester as a yellow powder. MS: 397 (M--C4H9O)+.

Workup

  1. customwas prepared
  2. waitat room temperature for 1 hour
  3. additionThe reaction mixture was then poured onto ice
  4. extractionextracted twice with 50 ml of ethyl acetate each time
  5. washThe combined organic extracts were washed with 50 ml of 3N hydrochloric acid and 50 ml of saturated sodium bicarbonate solution
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was purified by flash chromatography on 50 g of silica gel using
  9. additiona 10:1 mixture of methylene chloride and methanol as the eluting agent
  10. customto obtain there

Sources & evidence

ORD record
ord-9cf40b3bc4854259b875bbdb07d598ee
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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