1,2-Dichloroethane → HCID 69655948、化合物

HRID 857797ノート

反応式

HRID 857797 の反応式
C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.[C:15]([O:19][C:20]([NH:22][C@H:23]([CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)[C:24]([N:26]1[CH2:33][CH2:32][CH2:31][C@H:27]1[C:28](O)=[O:29])=[O:25])=[O:21])([CH3:18])([CH3:17])[CH3:16].[Cl:40][C:41]1[CH:42]=[CH:43][C:44]([C:49]2[N:50]=[N:51][S:52][CH:53]=2)=[C:45]([CH2:47][NH2:48])[CH:46]=1>CN(C=O)C>[C:15]([O:19][C:20]([NH:22][C@H:23]([CH:34]1[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]1)[C:24]([N:26]1[CH2:33][CH2:32][CH2:31][C@H:27]1[C:28]([NH:48][CH2:47][C:45]1[CH:46]=[C:41]([Cl:40])[CH:42]=[CH:43][C:44]=1[C:49]1[N:50]=[N:51][S:52][CH:53]=1)=[O:29])=[O:25])=[O:21])([CH3:18])([CH3:16])[CH3:17]

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 99754321-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethanoyl}-L-prolineHCID 21866164HCID 21866164、化合物

生成物 1

HCID 69655948HCID 69655948、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

EDC (0.388 g, 2.02 mmol), HOAt (0.275 g, 2.02 mmol), and 1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethanoyl}-L-proline (prepared by standard peptide coupling protocols, 0.551 g, 1.55 mol) were added to a stirred solution of 1-[5-Chloro-2-(1,2,3-thiadiazol-4-yl)phenyl]methanamine (0.351 g, 1.555 mmol) in DMF (7.8 mL). After 16 h the mixture was partitioned between EtOAc and water. The organic layer was washed with brine, dried (Na2SO4) and concentrated in vacuo. The product was purified by flash chromatography on silica (eluting with an EtOAc/hexanes gradient, 1–100% EtOAc). 1-{(2R)-2-[(tert-Butoxycarbonyl)amino]-2-cyclohexylethanoyl}-N-[5-chloro-2-(1,2,3-thiadiazol-4-yl)benzyl]-L-prolinamide was obtained as a solid. MS m/z=562.6.

後処理

  1. customAfter 16 h the mixture was partitioned between EtOAc and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by flash chromatography on silica (
  6. washeluting with an EtOAc/hexanes gradient, 1–100% EtOAc)

出典と根拠

ORDレコード
ord-55a0449bf4944b68aca1df815e48c9fc
出典データセット
uspto-grants-2006_12
特許番号
US07144899B2

反応ノート

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