Carbon Dioxide → N-CBZ-D-phenylalanyl-L-valyl-L-alanine

HRID 345221ノート

反応式

HRID 345221 の反応式
[CH2:1](N(CC)CC)C.[NH:8]1C[CH2:19][CH2:18][C@H:9]1[C:10]([NH:12][C@H:13]([C:15]([OH:17])=[O:16])[CH3:14])=[O:11].C(=O)=O.[N+](C1C=CC(O[C:34](=[O:54])[C@@H:35]([CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[NH:36][C:37]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:38])=CC=1)([O-])=O.Cl>O1CCOCC1.O.C(OCC)(=O)C>[C:37]([NH:36][C@@H:35]([C:34]([NH:8][C@H:9]([C:10]([NH:12][C@H:13]([C:15]([OH:17])=[O:16])[CH3:14])=[O:11])[CH:18]([CH3:19])[CH3:1])=[O:54])[CH2:47][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)([O:39][CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)=[O:38]

参加物

8

反応物 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 6347578L-Prolyl-L-alanineHCID 12448569N-((Phenylmethoxy)carbonyl)-D-phenylalanine 4-nitrophenyl ester

生成物 1

HCID 18647210N-CBZ-D-phenylalanyl-L-valyl-L-alanine収率 69%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 218864351,4-Dioxane--water (1/1)溶媒

実験手順

Triethylamine (9.0 mmol, 1.25 mL) was added to a mixture of L-prolyl-L-alanine (Sigma, 4.5 mmol, 838 mg) in 80 mL of 1:1 dioxane-water. After 15 minutes, pieces of solid carbon dioxide were added to the solution until the pH was reduced to pH 8. N-CBZ-D-Phenylalanine 4-nitrophenyl ester (Sigma, 4.5 mmol, 1.89 g) was then added, and the mixture was stirred at room temperature for four days. The clear yellow solution was acidified by gradual addition of 1 N HCl, and diluted with ethyl acetate. The organic phase was then separated, washed with water (3×) and brine (2×), dried (MgSO4), and rotary evaporated to give an oil residue. A solution of this residue in ethyl acetate was fractionally extracted with three solutions of 80 mg NaHCO3 in 10 mL water. These aqueous extracts were combined, acidified, and extracted with ethyl acetate. The resulting ethyl acetate solution was washed with brine, dried (MgSO4), evaporated, and dried at high vacuum to provide 1.45 g (69%) of N-CBZ-D-phenylalanyl-L-valyl-L-alanine as a viscous oil, in sufficient purity for the next step.

後処理

  1. customThe organic phase was then separated
  2. washwashed with water (3×) and brine (2×)
  3. dry with materialdried (MgSO4)
  4. customrotary evaporated
  5. customto give an oil residue
  6. extractionA solution of this residue in ethyl acetate was fractionally extracted with three solutions of 80 mg NaHCO3 in 10 mL water
  7. extractionextracted with ethyl acetate
  8. washThe resulting ethyl acetate solution was washed with brine
  9. dry with materialdried (MgSO4)
  10. customevaporated
  11. customdried at high vacuum

出典と根拠

ORDレコード
ord-e2399fc19bcb4ba2adc60f24b2a41109
出典データセット
uspto-grants-1991_10
特許番号
US05055451

反応ノート

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