4-Nitrobenzoic Acid → (6S,7R)-2,2,3,3,11,11-hexamethyl-9-oxo-7-phenyl-4,10-dioxa-8-aza-3-siladodecan-6-yl 4-nitrobenzoate

HRID 64435ノート

反応式

HRID 64435 の反応式
[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C@@H:9]([OH:19])[CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:46]([C:49]1[CH:57]=[CH:56][C:52]([C:53](O)=[O:54])=[CH:51][CH:50]=1)([O-:48])=[O:47].N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(C)C=CC=CC=1>C1COCC1.C(OCC)(=O)C.O>[N+:46]([C:49]1[CH:50]=[CH:51][C:52]([C:53]([O:19][C@@H:9]([C@@H:8]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:7][C:6](=[O:26])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][O:11][Si:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[CH3:18])=[O:54])=[CH:56][CH:57]=1)([O-:48])=[O:47]

参加物

8

反応物 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 10738641tert-butyl[(1R,2R)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxy-1-phenylpropyl]carbamateHCID 66880968DIAD toluene

生成物 1

HCID 86713450(6S,7R)-2,2,3,3,11,11-hexamethyl-9-oxo-7-phenyl-4,10-dioxa-8-aza-3-siladodecan-6-yl 4-nitrobenzoate収率 65.5%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 700 mg of tert-butyl[(1R,2R)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxy-1-phenylpropyl]carbamate in 35 ml of THF was added 1.2 g of triphenylphosphine, 766 mg of 4-nitrobenzoic acid, and 2.4 ml of a 1.9 M diisopropyl azodicarboxylate/toluene solution under ice-cooling, followed by stirring at room temperature for 5 hours. To the reaction mixture were added water and ethyl acetate to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 638 mg of (6S,7R)-2,2,3,3,11,11-hexamethyl-9-oxo-7-phenyl-4,10-dioxa-8-aza-3-siladodecan-6-yl 4-nitrobenzoate.

後処理

  1. temperaturecooling
  2. customa layer separation operation
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-3400f52d25304f91b1f8c251a22a3f58
出典データセット
uspto-grants-2016_09
特許番号
US09447090B2

反応ノート

読み込み中…