1,2-Dichloroethane → HCID 44600522、化合物

HRID 882754ノート

反応式

HRID 882754 の反応式
[C:1]([N:8]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:9]1[C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[CH:18]1([N:22]2[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH2:21][CH2:20][CH2:19]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C.C([O-])(O)=O.[Na+]>[C:4]([O:3][C:1]([N:8]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:9]1[C:10]([N:25]1[CH2:26][CH2:27][CH2:28][N:22]([CH:18]2[CH2:19][CH2:20][CH2:21]2)[CH2:23][CH2:24]1)=[O:12])=[O:2])([CH3:5])([CH3:6])[CH3:7]

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acidHCID 69002457HCID 69002457、化合物

生成物 1

HCID 44600522HCID 44600522、化合物収率 56.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of N-Boc-trans-4-hydroxy-L-proline (1.0 g, 4.32 mmol), 1-cyclobutyl-[1,4]diazepane hydrochloride (981 mg, 4.32 mmol), EDC (869 mg, 4.54 mmol) and HOBt (583 mg, 4.32 mmol) in DMF (22 mL) was added Et3N (1.2 mL, 8.64 mmol). The solution was allowed to stir overnight at room temperature (rt). The mixture was diluted with 5% aqueous (aq.) NaHCO3 and extracted with CH2Cl2 (3×). The combined organic layers were dried and concentrated. Purification by FCC provided the desired product (897 mg, 56%). MS (ESI): mass calcd. for C19H33N3O4, 367.25; m/z found, 368.6 [M+H]+. 1H NMR (CDCl3): 4.81-4.67 (m, 1H), 4.59-4.48 (m, 1H), 3.79-3.42 (m, 6H), 2.92-2.80 (m, 1H), 2.63-2.30 (m, 4H), 2.26-2.07 (m, 2H), 2.07-1.97 (m, 3H), 1.91-1.75 (m, 4H), 1.73-1.54 (m, 2H), 1.48-1.39 (m, 9H).

後処理

  1. extractionextracted with CH2Cl2 (3×)
  2. customThe combined organic layers were dried
  3. concentrationconcentrated
  4. customPurification by FCC

出典と根拠

ORDレコード
ord-de35d3d59a19417e8baad5682117db88
出典データセット
uspto-grants-2012_08
特許番号
US08236792B2

反応ノート

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