Triethylamine → (2R,4S)-tert-Butyl 2-(dimethylcarbamoyl)-4-(2-(2-methoxyphenyl)quinazolin-4-ylamino)pyrrolidine-1-carboxylate

HRID 2189212ノート

反応式

HRID 2189212 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:30][CH3:31])[N:15]=2)[CH2:10][C@@H:9]1[C:32]([OH:34])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:36][NH:37][CH3:38].[B-](F)(F)(F)F.CN(C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)C.C(N(CC)CC)C>CN(C=O)C.O>[CH3:36][N:37]([CH3:38])[C:32]([C@H:9]1[CH2:10][C@H:11]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:30][CH3:31])[N:15]=2)[CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:34]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67366705(2R,4S)-1-(tert-Butoxycarbonyl)-4-(2-(2-methoxyphenyl)quinazolin-4-ylamino)pyrrolidine-2-carboxylic acid

生成物 1

HCID 67366947(2R,4S)-tert-Butyl 2-(dimethylcarbamoyl)-4-(2-(2-methoxyphenyl)quinazolin-4-ylamino)pyrrolidine-1-carboxylate収率 90%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of (2R,4S)-1-(tert-butoxycarbonyl)-4-(2-(2-methoxyphenyl)quinazolin-4-ylamino)pyrrolidine-2-carboxylic acid (0.095 g, 0.204 mmol), dimethylamine hydrochloride (0.017 g, 0.204 mmol), 0-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.077 g, 0.204 mmol), and triethylamine (0.037 mL, 0.265 mmol) in DMF (1 mL) was stirred for 24 hours. Water (20 mL) was added and the aqueous layer was extracted with ethyl acetate (3×20 mL). The organic extracts were combined, dried (MgSO4) and concentrated. Purification by silica gel chromatography (10% methanol in dichloromethane) gave the title compound as a solid (0.090 g, 90%).

後処理

  1. extractionthe aqueous layer was extracted with ethyl acetate (3×20 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (10% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-cf4c8a443031465dadbd2fc3034c041c
出典データセット
uspto-grants-2012_12
特許番号
US08324226B2

反応ノート

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