Diisopropylethylamine → (2,4-Bis-benzyloxy-5-isopropenyl-phenyl)-[4-(3-morpholin-4-yl-propoxy)-1,3-dihydro-isoindol-2-yl]-methanone

HRID 41435

反応式

HRID 41435 の反応式
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]([C:26]([CH3:28])=[CH2:27])=[CH:14][C:10]=1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.[N:62]1([CH2:68][CH2:69][CH2:70][O:71][C:72]2[CH:80]=[CH:79][CH:78]=[C:77]3[C:73]=2[CH2:74][NH:75][CH2:76]3)[CH2:67][CH2:66][O:65][CH2:64][CH2:63]1>C(Cl)Cl.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:15]([C:26]([CH3:28])=[CH2:27])=[CH:14][C:10]=1[C:11]([N:75]1[CH2:74][C:73]2[C:77](=[CH:78][CH:79]=[CH:80][C:72]=2[O:71][CH2:70][CH2:69][CH2:68][N:62]2[CH2:67][CH2:66][O:65][CH2:64][CH2:63]2)[CH2:76]1)=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 469151864-(3-Morpholin-4-yl-propoxy)-2,3-dihydro-1H-isoindoleHCID 498640162,4-Bis(benzyloxy)-5-isopropenylbenzoic acid

生成物 1

HCID 46915345(2,4-Bis-benzyloxy-5-isopropenyl-phenyl)-[4-(3-morpholin-4-yl-propoxy)-1,3-dihydro-isoindol-2-yl]-methanone

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 2,4-bis-benzyloxy-5-isopropenyl-benzoic acid (210 mg, 0.56 mmol) and diisopropylethylamine (0.25 mL, 1.4 mmol) in DCM (5 mL) was treated with bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBrOP) (287 mg, 0.62 mmol). After 1 hour a solution of 4-(3-morpholin-4-yl-propoxy)-2,3-dihydro-1H-isoindole (0.56 mmol, assuming a quantitative yield from the preceding step (C18)) in DCM (5 mL) was added. After 4 hours the mixture was diluted with ethyl acetate and washed with water, 1N sodium hydroxide solution and brine. The organic phase was dried (MgSO4) and concentrated to give a residue which was absorbed onto an SCX column. This was washed with 10% methanol/DCM then the product was eluted with 25% 2M methanolic ammonia/DCM) to afford an impure sample of the intermediate (2,4-bis-benzyloxy-5-isopropenyl-phenyl)-[4-(3-morpholin-4-yl-propoxy)-1,3-dihydro-isoindol-2-yl]-methanone.

後処理

  1. additionwas added
  2. washwashed with water, 1N sodium hydroxide solution and brine
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated
  5. customto give a residue which
  6. customwas absorbed onto an SCX column
  7. washThis was washed with 10% methanol/DCM
  8. washthe product was eluted with 25% 2M methanolic ammonia/DCM)

出典と根拠

ORDレコード
ord-552b91e5d4b04b68a14f51c878c6631d
出典データセット
uspto-grants-2013_09
特許番号
US08530469B2

関連ノート

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