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Triethylamine → di(tert-butyl) 2-({[1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indol-7-yl]sulfonyl}amino)ethyl phosphate

HRID 2238448
ノート
印刷プレビュー

反応式

HRID 2238448 の反応式
[P:1]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])([O:3][CH2:4][CH2:5][NH2:6])=[O:2].CCN(CC)CC.[Cl:24][CH2:25][CH:26]1[C:34]2[C:33]3[CH:35]=[CH:36][C:37]([S:39](Cl)(=[O:41])=[O:40])=[CH:38][C:32]=3[C:31]([N+:43]([O-:45])=[O:44])=[CH:30][C:29]=2[N:28](C(=O)C(F)(F)F)[CH2:27]1.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.O.CO>[P:1]([O:3][CH2:4][CH2:5][NH:6][S:39]([C:37]1[CH:36]=[CH:35][C:33]2[C:34]3[CH:26]([CH2:25][Cl:24])[CH2:27][NH:28][C:29]=3[CH:30]=[C:31]([N+:43]([O-:45])=[O:44])[C:32]=2[CH:38]=1)(=[O:41])=[O:40])([O:7][C:8]([CH3:10])([CH3:9])[CH3:11])([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:2]
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 4

HCID 8471TriethylamineHCID 10796Cesium carbonateHCID 862404572-Aminoethyl di(tert-butyl) phosphateHCID 866202591-(chloromethyl)-5-nitro-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole-7-sulfonyl chloride

生成物 1

HCID 54762391di(tert-butyl) 2-({[1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indol-7-yl]sulfonyl}amino)ethyl phosphate
収率 91%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of amine 226 (203 mg, 0.80 mmol) and Et3N (0.11 mL, 0.80 mmol) in THF (2 mL) was added to solution of 116 (306 mg, 0.67 mmol) in THF (8 mL) at 0° C. After 5 min the cooling bath was removed and after 10 min Cs2CO3 (0.44 g, 1.3 mmol) and MeOH (4 mL) were added. After a further 25 min the mixture was diluted with water and extracted with CH2C2 (×3). The combined extracts were dried and evaporated and the residue was purified by chromatography, eluting with EtOAc/petroleum ether (1:1 then 2:1) to give di(tert-butyl) 2-({[1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indol-7-yl]sulfonyl}amino)ethyl phosphate (227) (351 mg, 91%) as a red-orange foam: 1H NMR [(CD3)2SO] δ 8.59 (d, J=1.6 Hz, 1H), 8.04 (d, J=8.9 Hz, 1H), 7.95 (br s, 1H, 7.79 (dd, J=8.9, 1.8 Hz, 1H, 7.77 (s, 1H), 6.74 (s, 1H), 4.28-4.20 (m, 1H), 3.95-3.86 (m, 2H), 3.83-3.72 (m, 4H), 2.99 (t, J=6.0 Hz, 2H), 1.35 (s, 18H). HMS (FAB) calcd. for C23H3335ClN3O8PS (M+) m/z 577.1415, found 577.1412.

後処理

  1. additionwere added
  2. extractionextracted with CH2C2 (×3)
  3. customThe combined extracts were dried
  4. customevaporated
  5. customthe residue was purified by chromatography
  6. washeluting with EtOAc/petroleum ether (1:1

出典と根拠

ORDレコード
ord-a7804a1ec06b464ea2a9f008cc03ca20
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07718688B2

反応ノート

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