Triethylamine → tert-butyl 4-{3-[(3R)-3-({(1S)-1-[5-(benzyloxy)pyridin-3-yl]-3-tert-butoxy-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate

HRID 526375ノート

反応式

HRID 526375 の反応式
[NH2:1][C@H:2]([C:11]1[CH:12]=[N:13][CH:14]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=1)[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].O=C1CCC(=O)N1[O:32][C:33]([C@@H:35]1[CH2:40][CH2:39][CH2:38][N:37]([C:41](=[O:57])[CH2:42][CH2:43][CH:44]2[CH2:49][CH2:48][N:47]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:46][CH2:45]2)[CH2:36]1)=O.C(N(CC)CC)C>CN(C=O)C.ClCCl>[CH2:18]([O:17][C:15]1[CH:16]=[C:11]([C@@H:2]([NH:1][C:33]([C@@H:35]2[CH2:40][CH2:39][CH2:38][N:37]([C:41](=[O:57])[CH2:42][CH2:43][CH:44]3[CH2:49][CH2:48][N:47]([C:50]([O:52][C:53]([CH3:55])([CH3:54])[CH3:56])=[O:51])[CH2:46][CH2:45]3)[CH2:36]2)=[O:32])[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH:12]=[N:13][CH:14]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 71268086tert-butyl (3S)-3-amino-3-(5-phenylmethoxypyridin-3-yl)propanoateHCID 89407588tert-butyl 4-{3-[(3R)-3-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate

生成物 1

HCID 71258943tert-butyl 4-{3-[(3R)-3-({(1S)-1-[5-(benzyloxy)pyridin-3-yl]-3-tert-butoxy-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To tert-butyl (3S)-3-amino-3-[5-(benzyloxy)pyridin-3-yl]propanoate (1.15 g, 3.5 mmol) in DMF (13.4 mL) was added tert-butyl 4-{3-[(3R)-3-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate and triethylamine (1.46 mL, 10.5 mmol) in dichloromethane (13.5 mL) at 0° C. After 3 hours the mixture was quenched by addition of saturated aqueous ammonium chloride solution, phases were separated and the aqueous phase was extracted with diethyl ether. Combined organic extracts were dried over sodium sulphate, concentrated under reduced pressure and the residue was purified by chromatography on silica gel (ethyl acetate in hexane, 20 to 100% followed by methanol in ethyl acetate 0 to 20%) to yield 1.76 g tert-butyl 4-{3-[(3R)-3-({(1S)-1-[5-(benzyloxy)pyridin-3-yl]-3-tert-butoxy-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate.

後処理

  1. customAfter 3 hours the mixture was quenched by addition of saturated aqueous ammonium chloride solution, phases
  2. customwere separated
  3. extractionthe aqueous phase was extracted with diethyl ether
  4. dry with materialCombined organic extracts were dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by chromatography on silica gel (ethyl acetate in hexane, 20 to 100% followed by methanol in ethyl acetate 0 to 20%)

出典と根拠

ORDレコード
ord-32c3f8ca8d3b415185a50a2738797105
出典データセット
uspto-grants-2016_05
特許番号
US09345793B2

反応ノート

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