4-Methylmorpholine → Boc-Ile-Pro-OBzl

HRID 1655307ノート

反応式

HRID 1655307 の反応式
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=O)[C@H:3]([CH2:5][CH3:6])[CH3:4].CN1CCOCC1.C(OC(Cl)=O)C(C)C.C1C=CC2N(O)N=NC=2C=1.[NH:42]1[CH2:56][CH2:55][CH2:54][C@H:43]1[C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45].C([O-])(O)=O.[Na+]>CN(C=O)C>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([N:42]1[CH2:56][CH2:55][CH2:54][C@H:43]1[C:44]([O:46][CH2:47][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)=[O:45])=[O:9])[C@H:3]([CH2:5][CH3:6])[CH3:4]

参加物

8

反応物 6

HCID 79724-Methylmorpholine2 回HCID 62365Isobutyl chloroformateHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 736155Benzyl L-prolinateHCID 2724762tert-Butoxycarbonyl-L-isoleucine

生成物 1

HCID 14306235Boc-Ile-Pro-OBzl収率 92%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
-15 °C

実験手順

Boc-Ile-OH (12.01 g. 0.05 mole) in DMF (50 ml) was cooled to 0° C. and NMM (5.49 ml) was added. After cooling the solution to -15° C. isobutylchloroformate (6.48 ml) was added slowly while maintaining the temperature at -15° C. and stirred for 10 minutes at which time HOBt (7.65 g) was added and stirring was continued for additional 10 minutes. A pre-cooled solution of HCL-H-Pro-OBzl (12.09 g. 0.05 mole) in DMF (50 ml) and NMM (5.49 ml) was added to the above solution and the completeness of the reaction was followed by TLC. The reaction mixture was poured into a cold saturated NaHCO3 solution and stirred for one hour. The peptide was extracted into CHCl3 and washed with acid and base (0.5N NaOH to remove HOBt), and on evaporting the solvent the product was obtained as an oil in 92% yield. Rf1, 0.65. Anal. Calcd. for C23H34N2O5 : C 66.00, H 9.19, N 6.69%. Found: C 65.58, H 8.28, N 7.13%.

後処理

  1. additionwas added slowly
  2. additionwas added
  3. stirringstirred for one hour
  4. extractionThe peptide was extracted into CHCl3
  5. washwashed with acid and base (0.5N NaOH to remove HOBt)
  6. customwas obtained as an oil in 92% yield

出典と根拠

ORDレコード
ord-137e904c749d4aeba6f16a766e365b3d
出典データセット
uspto-grants-1993_10
特許番号
US05250516

反応ノート

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