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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
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인쇄 미리보기

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HRID 722746 반응식
[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
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참가 물질

8

반응물 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23571419HCID 23571419, 화합물HCID 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

생성물 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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2b1d0af5ccaa4ae79d8240acc45d9a0e
출처 데이터셋
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07138395B2

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