4-Methylmorpholine → Boc-Val-Pro-Val-CF2CF3

HRID 613235ノート

反応式

HRID 613235 の反応式
[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:2]([C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)=[O:7])[CH:3]([CH3:5])[CH3:4].CN1CCOCC1.C(OC(Cl)=O)C(C)C.[NH2:38][C@H:39]([C:43]([C:45]([C:48]([F:51])([F:50])[F:49])([F:47])[F:46])=[O:44])[CH:40]([CH3:42])[CH3:41].Cl>C(Cl)Cl>[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:2]([C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([NH:38][C@H:39]([C:43]([C:45]([C:48]([F:49])([F:50])[F:51])([F:46])[F:47])=[O:44])[CH:40]([CH3:41])[CH3:42])=[O:12])=[O:7])[CH:3]([CH3:4])[CH3:5]

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 11045256Boc-Val-Pro-OHHCID 131719225H-Val-CF2CF3.hydrochloride

生成物 1

HCID 10075203Boc-Val-Pro-Val-CF2CF3収率 78.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-22 °C

実験手順

Dissolve Boc-Val-Pro-OH (314 mg, 1.0 mmol) in methylene chloride (4 mL) and add N-methylmorpholine (252 mg, 2.5 mmol). Cool to -22° C. and add isobutylchloroformate (136 mg, 1.0 mmol). Stir for 20 minutes and add to H-Val-CF2CF3.hydrochloride (1.1 mmol). Stir for 1 hour at -22° C., allow to warm to room temperature and stir for 3 hours. Purify by silica gel chromatography (40% ethyl acetate/hexane) to give the title compound (405 mg).

後処理

  1. stirringStir for 1 hour at -22° C.
  2. temperatureto warm to room temperature
  3. stirringstir for 3 hours
  4. customPurify by silica gel chromatography (40% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-fd4c5d42ec11417cbe03d8b89d6b69e6
出典データセット
uspto-grants-1999_12
特許番号
US06008196

反応ノート

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