Triethylamine → methyl (2R)-2-[(t-butoxycarbonyl)amino]-4-oxo-4-[4-(9H-thioxanthen-9-ylidene)-1-piperidinyl]butanoate

HRID 2374855ノート

反応式

HRID 2374855 の反応式
Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.[CH:20]1[C:33]2[C:32](=[C:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[S:25][C:24]=2[CH:23]=[CH:22][CH:21]=1.[C:40]([O:44][C:45]([NH:47][C@H:48]([C:53]([O:55][CH3:56])=[O:54])[CH2:49][C:50](O)=[O:51])=[O:46])([CH3:43])([CH3:42])[CH3:41].[Cl-].[NH4+]>ClCCl>[C:40]([O:44][C:45]([NH:47][C@H:48]([CH2:49][C:50](=[O:51])[N:37]1[CH2:38][CH2:39][C:34](=[C:32]2[C:33]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[S:25][C:26]3[C:31]2=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:35][CH2:36]1)[C:53]([O:55][CH3:56])=[O:54])=[O:46])([CH3:43])([CH3:42])[CH3:41]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11021202(3S)-3-(((tert-butoxy)carbonyl)amino)-4-methoxy-4-oxobutanoic acidHCID 130525974-(9H-thioxanthen-9-ylidene)piperidine

生成物 1

HCID 86594136methyl (2R)-2-[(t-butoxycarbonyl)amino]-4-oxo-4-[4-(9H-thioxanthen-9-ylidene)-1-piperidinyl]butanoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1.00 g (5.22 mmol) of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride, 0.73 ml (5.24 mmol) of triethylamine and 1.351 g (4.84 mmol) of 4-(9H-thioxanthen-9-ylidene)piperidine were added to 1.290 g (5.22 mmol) of (S)-3-[(t-butoxycarbonyl)amino]-4-methoxy-4-oxobutanoic acid in 20 ml of dichloromethane in an ice bath, and they were stirred at room temperature overnight. Saturated aqueous ammonium chloride solution was added to the reaction mixture. After extracting with dichloromethane, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by the silica gel chromatography (hexane:ethyl acetate=7:3 to 1:1) to obtain the title compound.

後処理

  1. extractionAfter extracting with dichloromethane
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by the silica gel chromatography (hexane:ethyl acetate=7:3 to 1:1)

出典と根拠

ORDレコード
ord-1651d709d5b5465b97d9be3af5a605f8
出典データセット
uspto-grants-2008_12
特許番号
US07462630B2

反応ノート

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