Citric Acid → Boc-Lys(Z)-Leu-Leu-OH

HRID 849695ノート

反応式

HRID 849695 の反応式
[NH:1]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C@H:2]([C:18]([NH:20][C@H:21]([C:26]([NH:28][C@H:29]([C:34]([O:36]C)=[O:35])[CH2:30][CH:31]([CH3:33])[CH3:32])=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CC(C)=O.O>[NH:1]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C@H:2]([C:18]([NH:20][C@H:21]([C:26]([NH:28][C@H:29]([C:34]([OH:36])=[O:35])[CH2:30][CH:31]([CH3:32])[CH3:33])=[O:27])[CH2:22][CH:23]([CH3:24])[CH3:25])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]

参加物

6

反応物 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 12020545HCID 12020545、化合物

生成物 1

HCID 12020555Boc-Lys(Z)-Leu-Leu-OH

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒2 回

実験手順

Boc-Lys(Z)-Leu-Leu-OMe (12.0 g, 19.33 mmol) was dissolved in acetone (41.0 g, 52 mL) at 22-23° C. A solution of NaOH (1.94 g, 48.5 mmol) in water (18.0 g) was added over 5 min. After stirring for 40 min., the reaction was quenched with a solution of citric acid (10.2 g, 53.0 mmol) in water (18.0 g). The acetone was removed on a rotary evaporator at 40° C. The remaining mixture was extracted with ethyl acetate (2×65 mL). The EtOAc extract was washed with water (50 g) then with aqueous saturated sodium chloride solution (50 g). The EtOAc extract was dried over anhydrous MgSO4 (10 g). The EtOAc solution was filtered and diluted with DMF (40 g). The ethyl acetate was evaporated at 40° C. under reduced pressure to give the solution of the product in DMF. Weight of solution ~52 g.

後処理

  1. customThe acetone was removed on a rotary evaporator at 40° C
  2. extractionThe remaining mixture was extracted with ethyl acetate (2×65 mL)
  3. extractionThe EtOAc extract
  4. washwas washed with water (50 g)
  5. extractionThe EtOAc extract
  6. dry with materialwas dried over anhydrous MgSO4 (10 g)
  7. filtrationThe EtOAc solution was filtered
  8. additiondiluted with DMF (40 g)
  9. customThe ethyl acetate was evaporated at 40° C. under reduced pressure
  10. customto give the solution of the product in DMF

出典と根拠

ORDレコード
ord-1bbf97f4c9e64646940a284135632816
出典データセット
uspto-grants-2000_01
特許番号
US06013764

反応ノート

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