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Triphenylphosphine → 1-(2-Morpholin-2-ylethyl)-3-phenyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

HRID 1818820
ノート
印刷プレビュー

反応式

HRID 1818820 の反応式
[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[NH:9][S:8]2(=[O:17])=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:38][CH2:39][CH:40]1[O:45][CH2:44][CH2:43][N:42](C(OC(C)(C)C)=O)[CH2:41]1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[NH:42]1[CH2:43][CH2:44][O:45][CH:40]([CH2:39][CH2:38][N:9]2[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[S:8]2(=[O:16])=[O:17])[CH2:41]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 44182317tert-Butyl 2-(2-hydroxyethyl)morpholine-4-carboxylateHCID 468330931-Phenyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

生成物 1

HCID 547569241-(2-Morpholin-2-ylethyl)-3-phenyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-phenyl-1,3-dihydro-2,1,3-benzothiadiazole2,2-dioxide (0.2 g, 0.8 mmol) in THF (10 mL) was added triphenylphosphine (0.26 g, 1 mmol), tert-butyl 2-(2-hydroxyethyl)morpholine-4-carboxylate (0.2 g, 0.9 mmol) and DIAD (0.2 g, 1 mmol) at 0° C. The mixture was allowed to warm to ambient temperature overnight then concentrated and chromatographed on silica gel (0 to 40% EtOAC in hexane). The resulting mostly pure carbamate was dissolved in dichloromethane (10 mL) and treated with HCL (4 mL, 4M in dioxane). The resulting salt was chromatographed on silica (0 to 100% of (7N NH3/MeOH) in dichloromethane) giving the desired product as a clear oil (0.23 g, 80%). HRMS: calcd for C18H21N3O3S+H+, 360.1376; found (ESI, [M+H]+), 360.1377.

後処理

  1. concentrationthen concentrated
  2. customchromatographed on silica gel (0 to 40% EtOAC in hexane)
  3. dissolutionThe resulting mostly pure carbamate was dissolved in dichloromethane (10 mL)
  4. additiontreated with HCL (4 mL, 4M in dioxane)
  5. customThe resulting salt was chromatographed on silica (0 to 100% of (7N NH3/MeOH) in dichloromethane)

出典と根拠

ORDレコード
ord-925fb8f9c4614bedbce2345bbef1660d
出典データセット
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07601722B2

反応ノート

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