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Ammonium Chloride → HCID 69211802、化合物

HRID 902911
ノート
印刷プレビュー

反応式

HRID 902911 の反応式
[Li+].CC([N-]C(C)C)C.[CH2:9]([O:11][C:12](=[O:37])[CH2:13][CH2:14][CH2:15][CH2:16][S:17][C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:10].Br[CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41].[Cl-].[NH4+]>C1COCC1.CCOCC.CN(P(N(C)C)(N(C)C)=O)C>[CH2:9]([O:11][C:12](=[O:37])[CH:13]([CH2:14][CH2:15][CH2:16][S:17][C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH3:10]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 79177tert-Butyl bromoacetateHCID 2724682Lithium diisopropylamideHCID 69224758HCID 69224758、化合物

生成物 1

HCID 69211802HCID 69211802、化合物

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒
HCID 8028
Tetrahydrofuran
溶媒
2 回
HCID 12679Hexamethylphosphoramide溶媒

反応条件

温度
-40 °C

実験手順

To a solution of LDA (2M, 9.1 mL, 18.17 mmol) at −70° C. was added HMPA (10 mL) followed by the drop wise addition of a solution of the compound of example 27 (6.12 g, 15.14 mmol) in anhydrous THF (10 mL). The reaction mixture was allowed to warm up to −40° C. and was stirred for another 30 minutes, after which, a solution of tert-butyl bromoacetate (2.5 mL, 16.65 mmol) in anhydrous THF (10 mL) was added. The reaction mixture was stirred for 1 h at the same temperature and then allowed to warm up to room temperature followed by stirring for 24 h. The reaction mixture was portioned between ether and saturated ammonium chloride. The water phase was extracted several times with ether. The recombined organic layer was washed with brine, dried, filtered and evaporated. Silica gel chromatography using 5% ethyl acetate in hexanes provided the product as a light yellow oil. 1H-NMR(CDCl3, 400 MHz: 1.24(t, J=7.1 Hz, 3H); 1.43(s, 9H); 1.40-1.57(m, 4H); 2.15(m, 2H); 2.24(m, 1H); 2.58(m, 2H); 4.12(q, J=7.1 Hz, 2H), 7.19-7.23, 7.26-7.30, 7.41(m, 15H).

後処理

  1. stirringThe reaction mixture was stirred for 1 h at the same temperature
  2. temperatureto warm up to room temperature
  3. stirringby stirring for 24 h
  4. extractionThe water phase was extracted several times with ether
  5. washThe recombined organic layer was washed with brine
  6. customdried
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-6c39e74d9f7e4063870d0a2dee5cf64a
出典データセット
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07365091B2

反応ノート

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