1,2-Dichloroethane → N-[2(S)-(t-Butoxycarbonylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl)glycine methionine methyl ester

HRID 259969ノート

反応式

HRID 259969 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:27]([CH3:30])[CH2:28][CH3:29])[CH2:10][N:11]([CH2:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)[CH2:12][C:13]([OH:15])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.Cl.[CH3:46][O:47][C:48](=[O:55])[C@H:49]([CH2:51][CH2:52][S:53][CH3:54])[NH2:50].CCN(CC)CC>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:27]([CH3:30])[CH2:28][CH3:29])[CH2:10][N:11]([CH2:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)[CH2:12][C:13]([OH:15])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:46][O:47][C:48](=[O:55])[C@H:49]([CH2:51][CH2:52][S:53][CH3:54])[NH2:50]

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 22861722N-[2(S)-(t-Butoxycarbonylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl)glycine

生成物 1

HCID 67554562N-[2(S)-(t-Butoxycarbonylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl)glycine methionine methyl ester収率 100.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

N-[2(S)-(t-Butoxycarbonylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl)glycine (2.29 g, 5.53 mmol), dissolved in DMF (20 mL), was treated with HOBT (0.822 g, 6.08 mmol), EDC (1.17 g, 6.08 mmol), and methionine methyl ester hydrochloride (1.21 g, 6.08 mmol). The pH was adjusted to 7.5 with Et3N (1.7 mL, 12 mmol) and the mixture was stirred at ambient temperature for 24 h. The mixture was concentrated, and the residue was partitioned between EtOAc (50 mL) and saturated NaHCO3 solution (25 mL). The aqueous layer was extracted with EtOAc (1×30 mL). The organic layers were combined, washed with brine (1×25 mL), dried (Na2SO4), filtered, and concentrated to give 3.2 g of crude product which was purified by chromatography (silica gel eluting with 1:3 to 1:2 ethyl acetate in hexane) to give pure product. 1H NMR (CD3OD) δ8.33 (1H, d, J=6 Hz), 7.90 (1H, d, J=6 Hz), 7.82 (1H, d, J=6 Hz), 7.61-7.39 (4H, m), 6.60-6.52 (1H, m), 4.32-4.06 (2H, m), 3.90-3.69 (1H, m), 3.65 (3H, s), 3.27-3.14 (2H, m), 2.93-2.70 (2H, m), 2.19-1.78 (6H, m), 1.63-1.30 (13H, m), 1.19-1.05 (1H, m), 0.95-0.81 (6H, m) ppm.

後処理

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between EtOAc (50 mL) and saturated NaHCO3 solution (25 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (1×30 mL)
  4. washwashed with brine (1×25 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-b9454d2710924a3ba4883a030043c786
出典データセット
uspto-grants-1996_06
特許番号
US05523456

反応ノート

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