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Potassium Carbonate → (3-{(S)-5-[5-Chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-ylcarbamoyl}-oxetan-3-yl)-carbamic acid 9H-fluoren-9-ylmethyl ester

HRID 2046560
ノート
印刷プレビュー

反応式

HRID 2046560 の反応式
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C:19]3([C:23](O)=[O:24])[CH2:22][O:21][CH2:20]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[Cl:49][C:50]1[CH:51]=[C:52]([F:72])[C:53]([C:66]2[N:70]=[C:69]([CH3:71])[O:68][N:67]=2)=[C:54]([C:56]2[CH:57]=[C:58]3[C:62](=[CH:63][CH:64]=2)[C@@H:61]([NH2:65])[CH2:60][CH2:59]3)[CH:55]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:17])[NH:18][C:19]3([C:23](=[O:24])[NH:65][C@@H:61]4[C:62]5[C:58](=[CH:57][C:56]([C:54]6[CH:55]=[C:50]([Cl:49])[CH:51]=[C:52]([F:72])[C:53]=6[C:66]6[N:70]=[C:69]([CH3:71])[O:68][N:67]=6)=[CH:64][CH:63]=5)[CH2:59][CH2:60]4)[CH2:22][O:21][CH2:20]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 11430Potassium CarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 679511683-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)oxetane-3-carboxylic acidHCID 68296736(S)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-ylamine

生成物 1

HCID 68296802
(3-{(S)-5-[5-Chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-ylcarbamoyl}-oxetan-3-yl)-carbamic acid 9H-fluoren-9-ylmethyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of 3-(9H-fluoren-9-ylmethoxycarbonylamino)-oxetane-3-carboxylic acid (1.70 g, 5.01 mmol) in dry DMF (50.0 ml) were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.60 g, 8.35 mmol) and 1-hydroxybenzotriazole hydrate (0.95 g, 6.20 mmol) at room temperature. The resulting colorless solution was stirred for 10 min before a solution of (S)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-ylamine (1.64 g, 4.77 mmol, intermediate A-11) in dry DMF (2.0 ml) was added. This mixture was stirred at room temperature for 20 h. Then water was added, the pH was adjusted to 9 with sat. K2CO3 solution and the mixture was extracted twice with MeCl2. The combined organic layers were washed with water and brine, dried with MgSO4 and evaporated. The remaining light brown foam was purified by chromatography (silica gel; MeCl2/MeOH 100:0 to 98:2%) and the title compound was obtained as off white foam (3.17 g, 100%). MS: 665.2 (MH+, 1Cl).

後処理

  1. additionwas added
  2. extractionthe mixture was extracted twice with MeCl2
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried with MgSO4
  5. customevaporated
  6. customThe remaining light brown foam was purified by chromatography (silica gel; MeCl2/MeOH 100:0 to 98:2%)

出典と根拠

ORDレコード
ord-93dc9868eda341a28ede523e866941ba
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08592426B2

反応ノート

読み込み中…

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