1,2-Dichloroethane → HCID 9894399、化合物

HRID 1271079ノート

反応式

HRID 1271079 の反応式
[NH2:1][C@@H:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]([CH2:19][C:20]([F:23])([F:22])[F:21])[C:3]1=[O:24].[C:25]([C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[CH2:34][C:33]1([C:41](=[O:42])[NH:40][C:39](=[O:43])[NH:38]1)[CH2:32][CH2:31]2)(O)=[O:26].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[O:43]=[C:39]1[NH:38][C:33]2([CH2:32][CH2:31][C:30]3[C:35](=[CH:36][CH:37]=[C:28]([C:25]([NH:1][C@@H:2]4[N:8]=[C:7]([C:9]5[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=5)[C:6]5[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=5[N:4]([CH2:19][C:20]([F:21])([F:23])[F:22])[C:3]4=[O:24])=[O:26])[CH:29]=3)[CH2:34]2)[C:41](=[O:42])[NH:40]1

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 10854086HCID 10854086、化合物HCID 18440314(+/-)-6'-carboxy-3',4'-dihydro-1'H-spiro[imidazolidine-4,2'-naphthalene]-2,5-dione2 回

生成物 1

HCID 9894399HCID 9894399、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of (3R)-3-amino-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepine (Shi et al. Tetrahedron 1999, 55, 909) (507 mg, 1.52 mmol), (±)-6′-carboxy-3′,4′-dihydro-1′H-spiro[imidazolidine-4,2′-naphthalene]-2,5-dione (described in Intermediate 1) (396 mg, 1.52 mmol), EDC (438 mg, 2.28 mmol), HOBT (308 mg, 2.01 mmol), and N,N-diisopropylethylamine (0.795 mL, 4.56 mmol) was stirred in DMF (5 mL) at ambient temperature for 18 h. The crude mixture was partitioned between saturated aqueous NaHCO3 (25 mL) and CH2Cl2 (25 mL), and the aqueous phase was extracted further with CH2Cl2 (2×25 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated to dryness. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:0 to 95:5 to provide the title compound as an off-white solid. MS: m/z=576 (M+1). HRMS: m/z=576.1840; calculated m/z=576.1853 for C30H24F3N5 O4.

後処理

  1. customThe crude mixture was partitioned between saturated aqueous NaHCO3 (25 mL) and CH2Cl2 (25 mL)
  2. extractionthe aqueous phase was extracted further with CH2Cl2 (2×25 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of CH2Cl2

出典と根拠

ORDレコード
ord-a537a8565ae54c4284fe537c94006322
出典データセット
uspto-grants-2007_04
特許番号
US07205293B2

反応ノート

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