4-Methylmorpholine → tert-butyl-2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-[(2-pyrrol-1-yl)phenylcarbonylamino]-propionate

HRID 1760815ノート

反応式

HRID 1760815 の反応式
[C:1]([O:5][C:6](=[O:34])[C@H:7]([N:10]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]2[O:31][CH2:32][O:33][C:27]=2[CH:26]=1)[S:11]([C:14]1[C:19]([CH3:20])=[CH:18][C:17]([O:21][CH3:22])=[CH:16][C:15]=1[CH3:23])(=[O:13])=[O:12])[CH2:8][NH2:9])([CH3:4])([CH3:3])[CH3:2].[C:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[N:44]1[CH:48]=[CH:47][CH:46]=[CH:45]1)(O)=[O:36].O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.C(N=C=N)CC>CN(C)C1C=CN=CC=1.CN(C)C=O>[C:1]([O:5][C:6](=[O:34])[C@H:7]([N:10]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]2[O:31][CH2:32][O:33][C:27]=2[CH:26]=1)[S:11]([C:14]1[C:19]([CH3:20])=[CH:18][C:17]([O:21][CH3:22])=[CH:16][C:15]=1[CH3:23])(=[O:12])=[O:13])[CH2:8][NH:9][C:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[N:44]1[CH:48]=[CH:47][CH:46]=[CH:45]1)=[O:36])([CH3:4])([CH3:2])[CH3:3]

参加物

8

反応物 5

HCID 79724-MethylmorpholineHCID 7285212-(1H-pyrrol-1-yl)benzoic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 18621663Propyl carbodiimide hy-drochlorideHCID 69762296tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-amino-propionate

生成物 1

HCID 69762802tert-butyl-2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-[(2-pyrrol-1-yl)phenylcarbonylamino]-propionate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of tert-butyl-2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-amino-propionate (1.02 g, 2.0 mmol), 1-(2-carboxyphenyl)pyrrole (581 mg, 3.1 mmol), 1-hydroxybenzotriazole hydrate (279 mg, 2.0 mmol), N-methylmorpholine (0.8 ml, 7.3 mmol) and 4-dimethylaminopyridine (30 mg; 0.25 mmol) in dry dimethylformamide (25 ml) was added 1-ethyl-3,3-dimethylamino)-propyl carbodiimide hydrochloride salt (600 mg, 3.1 mmol) and the material was stirred overnight. The dimethylformamide was removed on the rotary evaporator and the residue was taken up in ethyl acetate (80 ml) and partitioned with an equal volume of aqueous hydrochloric acid (1.5%, 80 ml). The organic phase was collected and washed with equal volumes of 5% aqueous sodium bicarbonate and then brine. The aqueous phases were back extracted with ethyl acetate (2×80 ml) and the organic phases combined, dried over magnesium sulfate, filtered and condensed to provide a residue. This material was chromatographed using preparative TLC plates (45% ethyl acetate/hexanes) to afford tert-butyl-2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-[(2-pyrrol-1-yl)phenylcarbonylamino]-propionate) as a pale yellow foamy solid (927 mg).

後処理

  1. customThe dimethylformamide was removed on the rotary evaporator
  2. custompartitioned with an equal volume of aqueous hydrochloric acid (1.5%, 80 ml)
  3. customThe organic phase was collected
  4. washwashed with equal volumes of 5% aqueous sodium bicarbonate
  5. extractionThe aqueous phases were back extracted with ethyl acetate (2×80 ml)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customcondensed
  9. customto provide a residue
  10. customThis material was chromatographed

出典と根拠

ORDレコード
ord-432fd2de7649417e81fb197d2b551970
出典データセット
uspto-grants-2005_01
特許番号
US06844366B2

反応ノート

読み込み中…