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

HRID 467301노트

반응식

HRID 467301 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

HCID 18647210N-CBZ-D-phenylalanyl-L-valyl-L-alanine수율 69%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 218864351,4-Dioxane--water (1/1)용매

실험 절차

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 1N 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.

후처리

  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

출처 및 근거

ORD 기록
ord-5bbec666ba9f499198e933c8359b4ab7
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05158936

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