Ethylmorpholine → 2-(S)-[2-(S)-Allyloxycarbonylamino-3-(4-carbamimidoyl-phenyl)-propionylamino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester hydrochloride

HRID 1595141ノート

反応式

HRID 1595141 の反応式
[ClH:1].[CH2:2]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[NH:22])[NH2:21])=[CH:16][CH:15]=1)[C:10]([OH:12])=O)=[O:7])[CH:3]=[CH2:4].Cl.[CH3:24][O:25][C:26](=[O:38])[C@@H:27]([NH2:37])[CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(N1CCOCC1)C>CN(C=O)C>[ClH:1].[CH3:24][O:25][C:26](=[O:38])[C@@H:27]([NH:37][C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][CH2:2][CH:3]=[CH2:4])=[O:7])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[NH:22])[NH2:21])=[CH:16][CH:15]=1)[CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31]

参加物

6

反応物 4

HCID 7525EthylmorpholineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 16218751L-Glutamic acid, 5-(1,1-dimethylethyl) 1-methyl ester, hydrochloride (1:1)HCID 68613816(S)-2-Allyloxycarbonylamino-3-(4-carbamimidoylphenyl)propionic Acid Hydrochloride

生成物 1

HCID 686148872-(S)-[2-(S)-Allyloxycarbonylamino-3-(4-carbamimidoyl-phenyl)-propionylamino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester hydrochloride

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To 2-(S)allyloxycarbonylamino-3-(4-carbamimidoyl-phenyl)-propionic acid hydrochloride (3.48 g, 10.6 mmol) and 2-(S)-amino-pentanedioic acid 5-tert-butyl ester 1-methyl ester hydrochloride (2.7 g, 10.6 mmol) in 20 ml of DMF were added at −15° C. TOTU (3.83 g, 11.67 mmol) and N-ethylmorpholine (2.7 ml, 21.2 mmol). The mixture was stirred for 1 hour and then allowed to warm to room temperature. After evaporation, ethyl acetate was added to the residue and the organic layer was extracted with aqueous sodium hydrogen carbonate solution, potassium hydrogen sulfate solution, and water. The organic layer was evaporated. Yield: 2.8 g (50%). MS: m/z=491.3 (M+H)+.

後処理

  1. customAfter evaporation, ethyl acetate
  2. additionwas added to the residue
  3. extractionthe organic layer was extracted with aqueous sodium hydrogen carbonate solution, potassium hydrogen sulfate solution, and water
  4. customThe organic layer was evaporated

出典と根拠

ORDレコード
ord-645ee4743164483b94b7cfd67ecc2d21
出典データセット
uspto-grants-2001_09
特許番号
US06287794B1

反応ノート

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