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4-Methylmorpholine → {[2-{2-(S)-[Benzyloxy-carbonyl]-pyrrolidine-1-yl}-1-(R)-(4-methoxybenzyl)-2-oxo-ethyl]-tert.-butoxycarbonyl-amino}-acetic acid ethyl ester

HRID 1008579
ノート
印刷プレビュー

反応式

HRID 1008579 の反応式
Cl.[CH2:2]([O:9][C:10](=[O:16])[C@@H:11]1[CH2:15][CH2:14][CH2:13][NH:12]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:17]([O:19][C:20]([CH2:22][N:23]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@H:24]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[C:25](O)=[O:26])=[O:21])[CH3:18].CN1CCOCC1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O.O>[CH2:17]([O:19][C:20](=[O:21])[CH2:22][N:23]([C@H:24]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[C:25]([N:12]1[CH2:13][CH2:14][CH2:15][C@H:11]1[C:10]([O:9][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)=[O:16])=[O:26])[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH3:18]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2733413Proline benzyl ester hydrochlorideHCID 22958574n-Ethoxycarbonylmethyl-n-tert-butoxycarbonyl-2-(r)-amino-3-(4-methoxyphenyl)-propionic acid

生成物 1

HCID 69780750
{[2-{2-(S)-[Benzyloxy-carbonyl]-pyrrolidine-1-yl}-1-(R)-(4-methoxybenzyl)-2-oxo-ethyl]-tert.-butoxycarbonyl-amino}-acetic acid ethyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of (L)-proline benzyl ester hydrochloride (0.49 g), N-Ethoxycarbonylmethyl-N-tert.-butoxycarbonyl-2-(R)-amino-3-(4-methoxyphenyl)-propionic acid (0.760 g), N-methyl morpholine (0.93 mL) and 0.65 g of 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) in 10 mL of dry N,N-dimethyl formamide was stirred for 16 h at ambient temperature. The volatiles were pumped off and water was added followed by extraction with ethyl acetate and concentration of the organic layer. The remaining residue was purified by silica chromatography (isohexane/ethyl acetate 1/2). Yield: 0.99 g (86%); colorless oil; (+)-APCI-MS: 569 (MH+).

後処理

  1. extractionfollowed by extraction with ethyl acetate and concentration of the organic layer
  2. customThe remaining residue was purified by silica chromatography (isohexane/ethyl acetate 1/2)

出典と根拠

ORDレコード
ord-46b9abfb6aa14f0b8f7a56a86bde7f82
出典データセット
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06797710B2

反応ノート

読み込み中…

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