1,2-Dichloroethane → 3-Oxo-2-[2-(pyrimidin-2-ylamino)ethyl]-2,3-dihydro-1H-isoindole-5-carbonyl-2(S)phenylsulfonylamino-beta-alanine t-butyl ester

HRID 582690

反応式

HRID 582690 の反応式
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11](O)=[O:12])[CH:9]=2)[CH2:4][N:3]1[CH2:14][CH2:15][NH:16][C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1.Cl.[NH2:24][CH2:25][C@H:26]([NH:34][S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:37])=[O:36])[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[C:30]([O:29][C:27](=[O:28])[C@@H:26]([NH:34][S:35]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)(=[O:37])=[O:36])[CH2:25][NH:24][C:11]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[CH2:4][N:3]([CH2:14][CH2:15][NH:16][C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[C:2]2=[O:1])=[O:12])([CH3:33])([CH3:31])[CH3:32]

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 22853534(S)-3-amino-2-benzenesulfonylamino-propionic acid tert-butyl ester hydrochlorideHCID 701036023-Oxo-2-[2-(pyrimidin-2-ylamino)ethyl]-2,3-dihydro-1H-isoindole-5-carboylic acid

生成物 1

HCID 1317213113-Oxo-2-[2-(pyrimidin-2-ylamino)ethyl]-2,3-dihydro-1H-isoindole-5-carbonyl-2(S)phenylsulfonylamino-beta-alanine t-butyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A DMF solution (10 mL) of acid 6-4 (382 mg, 1.28 mmol) 1-4 (517 mg, 1.54 mmol), HOBT (264 mg, 1.13 mmol) NMM (563 μl, 5.1 mmol) and EDC (331 mg, 1.73 mmol) was stirred under ambient conditions for 18 h. The DMF was removed at 50° C. and the residue partitioned between EtOAc and H2O. The organic layer was washed with sat. NaHCO3 solution, brine, and dried (MgSO4). Evaporation gave a yellow foam which was purified by flash chromatography (silica, 3:1 acetone/CH2Cl2) to provide 6-5 as a colorless foam.

後処理

  1. customThe DMF was removed at 50° C.
  2. customthe residue partitioned between EtOAc and H2O
  3. washThe organic layer was washed with sat. NaHCO3 solution, brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation
  6. customgave a yellow foam which
  7. customwas purified by flash chromatography (silica, 3:1 acetone/CH2Cl2)

出典と根拠

ORDレコード
ord-01aea64beafc40a39d741df03c0dd7a8
出典データセット
uspto-grants-1999_07
特許番号
US05925655

関連ノート

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