4-Methylmorpholine → (R)-N-Benzyloxycarbonyl-alpha-{N-[(S)-1-(t-butoxycarbonyl)propyl]carbamoyl}-4-hydroxybenzylamine

HRID 719106ノート

反応式

HRID 719106 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:20]([OH:22])=O)[C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([O:27][C:28](=[O:33])[C@@H:29]([NH2:32])[CH2:30][CH3:31])([CH3:26])([CH3:25])[CH3:24].CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:20](=[O:22])[NH:32][C@H:29]([C:28]([O:27][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:33])[CH2:30][CH3:31])[C:13]1[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 1514128(R)-(N-Benzyloxycarbonyl)-p-hydroxyphenylglycineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 7019938(2S)-2-amino butanic acid t-butyl ester

生成物 1

HCID 69551129(R)-N-Benzyloxycarbonyl-alpha-{N-[(S)-1-(t-butoxycarbonyl)propyl]carbamoyl}-4-hydroxybenzylamine収率 63%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of (R)-N-benzyloxycarbonyl-α-carboxy-4-hydroxybenzylamine (Method 17; 2.00 g, 6.64 mmol), (2S)-2-amino butanoic acid t-butyl ester (1.30 g, 6.64 mmol) and N-methylmorpholine (2.0 g, 19.8 mmol) in DCM (30 ml) was stirred at RT for 5 min, after which TBTU (2.60 g, 8.10 mmol) was added. The reaction mixture was stirred at ambient temperature overnight. The solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel DCM:Acetone—60:40). The product was crystallized from toluene (20 ml) giving 1.85 g of the desired product as a white solid. NMR (400 MHz): 0.80 (3H, t), 1.45 (9H, s), 1.50–1.80 (2H, m), 4.10–4.20 (1H, m), 5.05 (1H, d(AB)), 5.15 (1H, d(AB)), 6.75 (2H, d), 7.20–7.40 (7H, m).

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatography on silica gel DCM
  3. customThe product was crystallized from toluene (20 ml)

出典と根拠

ORDレコード
ord-32fd5c3c8557459c8f1dfbcf94e1595e
出典データセット
uspto-grants-2006_11
特許番号
US07132416B2

反応ノート

読み込み中…