4-Methylmorpholine → HCID 12020545、化合物

HRID 849688ノート

反応式

HRID 849688 の反応式
ClC(OCC(C)C)=O.[NH:9]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@H:10]([C:26]([OH:28])=O)[CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].CN1CCOCC1.[NH2:43][C@H:44]([C:49]([NH:51][C@H:52]([C:57]([O:59][CH3:60])=[O:58])[CH2:53][CH:54]([CH3:56])[CH3:55])=[O:50])[CH2:45][CH:46]([CH3:48])[CH3:47].Cl>C(OCC)(=O)C>[NH:9]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@H:10]([C:26]([NH:43][C@H:44]([C:49]([NH:51][C@H:52]([C:57]([O:59][CH3:60])=[O:58])[CH2:53][CH:54]([CH3:55])[CH3:56])=[O:50])[CH2:45][CH:46]([CH3:47])[CH3:48])=[O:28])[CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17]

参加物

6

反応物 4

HCID 79724-Methylmorpholine2 回HCID 62365Isobutyl chloroformateHCID 2724765Boc-Lys(Z)-OHHCID 15598024L-Leucine, L-leucyl-, methyl ester, hydrochloride (1:1)

生成物 1

HCID 12020545HCID 12020545、化合物収率 90.2%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒7 回

実験手順

Isobutyl chloroformate (13.66 g, 100 mmol) was added dropwise over 15 min at -15 to -10° C. to a solution of Boc-Lys(Z)-OH (38.04 9, 100 mmol) in ethyl acetate (200 g). Another portion of ethyl acetate was added (10 g) and the mixture was stirred for 15 min. 4-Methylmorpholine (10.12 g, 100 mmol) was added dropwise over 15 min at -15 to -10° C., followed by an additional portion of ethyl acetate (10.0 g) and the resulting mixture was stirred for 2 h. In a separate reaction vessel 4-methylmorpholine (10.12 g, 100 mmol) was added dropwise over 15 min, to a solution of H-Leu-Leu-OMe·HCl (29.48 g, 100 mmol) in ethyl acetate (200.0 g) at -23 to -10° C. An additional portion of ethyl acetate (10.0 g) was added followed by the addition of the formed anhydride over 30 to 45 min at a temperature of -8 to -10° C. Another portion of ethyl acetate (30.0 g) was added and the resulting mixture was stirred for 1.5 h. Ethyl acetate (50.00 g) was added, the solution was filtered and the resulting organic filtrate was concentrated in vacuo. The resulting solid was recrystallized from petroleum ether (bp 100 to 125) to give Boc-Lys(Z)-Leu-Leu-OMe (55.9 g, 90.2%).

後処理

  1. stirringthe resulting mixture was stirred for 2 h
  2. stirringthe resulting mixture was stirred for 1.5 h
  3. filtrationthe solution was filtered
  4. concentrationthe resulting organic filtrate was concentrated in vacuo
  5. customThe resulting solid was recrystallized from petroleum ether (bp 100 to 125)

出典と根拠

ORDレコード
ord-d1f8416c182e40b0ad394d5b311fcde7
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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