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4-Methylmorpholine → 4-(tert-Butyl-dimethyl-silanyloxy)-3-({7-[(naphthalene-2-carbonyl)-amino]-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carbonyl}-amino)-butyric Acid Benzyl Ester

HRID 722746
ノート
印刷プレビュー

反応式

HRID 722746 の反応式
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:13][CH:14]1[C:21](=[O:22])[N:20]2[CH:23]([C:27](O)=[O:28])[CH2:24][CH2:25][CH2:26][CH:19]2[CH2:18][CH:17]=[CH:16][CH2:15]1)=[O:12].Cl.CN(C)CCCN=C=NCC.CN1CCOCC1.ON1C2C=CC=CC=2N=N1.[CH2:59]([O:66][C:67](=[O:80])[CH2:68][CH:69]([NH2:79])[CH2:70][O:71][Si:72]([C:75]([CH3:78])([CH3:77])[CH3:76])([CH3:74])[CH3:73])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>C1COCC1.O>[CH2:59]([O:66][C:67](=[O:80])[CH2:68][CH:69]([NH:79][C:27]([CH:23]1[N:20]2[C:21](=[O:22])[CH:14]([NH:13][C:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)=[O:12])[CH2:15][CH:16]=[CH:17][CH2:18][CH:19]2[CH2:26][CH2:25][CH2:24]1)=[O:28])[CH2:70][O:71][Si:72]([C:75]([CH3:76])([CH3:77])[CH3:78])([CH3:74])[CH3:73])[C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1
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 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23571419HCID 23571419、化合物HCID 696597087-[(Naphthalene-2-carbonyl)-amino]-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic acid

生成物 1

HCID 69659665
4-(tert-Butyl-dimethyl-silanyloxy)-3-({7-[(naphthalene-2-carbonyl)-amino]-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carbonyl}-amino)-butyric Acid Benzyl Ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

7-[(Naphthalene-2-carbonyl)-amino]-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic acid (0.44 gm) is dissolved in 15 mL THF to which 0.24 gm of 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (EDC), 0.15 mL of N-methylmorpholine, and 0.17 gm of 1-hydroxybenzotriazole (HOBt) is added. The reaction mixture is stirred for 20 min then added to a solution of 3-amino-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid benzyl ester (0.52 gm, prepared by methods described in Chem. Pharm. Bull. 1999, 47, 11–21) in 5 mL THF. The resulting mixture is striired at RT for ˜18 h, then poured into water, and extracted with ethyl acetate. The organic layer is washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, then dried over sodium sulfate powder. Filtration and evaporation produces a crude product which is then purified over silica (1:1 ethylacetate:hexanes) to afford the desired product.

後処理

  1. additionis added
  2. waitThe resulting mixture is striired at RT for ˜18 h
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate powder
  6. filtrationFiltration and evaporation
  7. customproduces a crude product which
  8. customis then purified over silica (1:1 ethylacetate:hexanes)

出典と根拠

ORDレコード
ord-2b1d0af5ccaa4ae79d8240acc45d9a0e
出典データセット
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07138395B2

反応ノート

読み込み中…

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