1,2-Dichloroethane → 1-(2-methoxy-4-(1-Boc-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide

HRID 128592ノート

反応式

HRID 128592 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH:6]=[CH:5][C:4]=1[CH2:23][C:24]([OH:26])=O.[CH3:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N:34]1[CH2:39][CH2:38][NH:37][CH:36]([C:40]([NH2:42])=[O:41])[CH2:35]1.C(Cl)CCl.C(N(CC)CC)C>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:12][CH2:11]2)[CH:6]=[CH:5][C:4]=1[CH2:23][C:24]([N:37]1[CH2:38][CH2:39][N:34]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[CH3:27])[CH2:35][CH:36]1[C:40]([NH2:42])=[O:41])=[O:26]

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 154305682-Carbamoyl-4-(2-methylphenyl)piperazineHCID 189141692-(4-(1-(Tert-butoxycarbonyl)piperidin-4-yloxy)-2-methoxyphenyl)acetic acid

生成物 1

HCID 189141921-(2-methoxy-4-(1-Boc-4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-Methoxy-4-(1-Boc-4-piperidyloxy)phenylacetic acid (331 mg, 0.91 mmol), 4-(2-methylphenyl)piperazine-2-carboxamide (200 mg, 0.91 mmol), EDC (209 mg, 1.09 mmol), and HBT (141 mg, 1.04 mmol) were combined in DMF (7 ml) under nitrogen. The mixture was adjusted to pH ca. 9 (moistened E. Merck colorpHast indicator) by addition of triethylamine (0.4 ml) and stirred at ambient temperature for 72 hours. The mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and aqueous sodium bicarbonate. The ethyl acetate layer was washed with. sodium bicarbonate and with brine, dried over sodium sulfate, filtered, and evaporated to dryness in vacuo. The residue was chromatographed on silica gel eluted with 3% methanol in methylene chloride. The combined product fractions were evaporated to dryness in vacuo to give 1-(2-methoxy-4-(1-Boc-4-piperdyloxy)phenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide.

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate
  3. washThe ethyl acetate layer was washed with
  4. dry with materialsodium bicarbonate and with brine, dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo
  7. customThe residue was chromatographed on silica gel
  8. washeluted with 3% methanol in methylene chloride
  9. customThe combined product fractions were evaporated to dryness in vacuo

出典と根拠

ORDレコード
ord-9072fb1685fc4f15899aa1b9bdcb5a30
出典データセット
uspto-grants-1995_11
特許番号
US05464788

反応ノート

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