Diisopropylethylamine → (3R)-3-methyltetrahydro-2H-pyrazino[1,2-a]pyrazine-1,4(3H,6H)-dione

HRID 421229

反応式

HRID 421229 の反応式
[C:1]([N:8]1[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH:9]1[C:21]([OH:23])=O)([O:3]C(C)(C)C)=O.CN(C(O[N:32]1N=N[C:34]2C=CC=C[C:33]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.Cl.COC(=O)[C@@H](C)N>ClCCl.CN(C=O)C>[CH3:34][C@@H:33]1[C:1](=[O:3])[N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH:9]2[C:21](=[O:23])[NH:32]1

参加物

7

反応物 4

HCID 81531Diisopropylethylamine2 回HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11182647Methyl D-alaninate hydrochlorideHCID 112559791,4-Di-Boc-piperazine-2-carboxylic acid

生成物 1

HCID 59215897(3R)-3-methyltetrahydro-2H-pyrazino[1,2-a]pyrazine-1,4(3H,6H)-dione

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of N,N′-diboc-piperazine-2-carboxylic acid (2 g, 6.06 mmol) in 50 mL of dichloromethane and was added TBTU (2.138 g, 6.66 mmol) and diisopropylethyl amine (1.3 mL, 7.26 mmol). The reaction was stirred for 45 min. In the meantime, a suspension of D-alanine methyl ester hydrochloride (1.249 g, 12.11 mmol) and diisopropylethylamine (3.27 mL, 18.76 mmol) in 20 mL of dichloromethane and 5 mL of DMF was stirred and finally added to the reaction mixture. The reaction was left stirring at room temperature overnight. UPLC-MS analysis showed the expected product (peak at 0.72 min, m/z=416 (M+1), 360 (M−t-Bu+1). The reaction was diluted with dichloromethane and extracted with sat. NaHCO3, dried (Na2SO4), and the solvent removed. The crude (4.242 g) was taken to the next step without further purification.

後処理

  1. stirringwas stirred
  2. additionfinally added to the reaction mixture
  3. waitThe reaction was left
  4. stirringstirring at room temperature overnight

出典と根拠

ORDレコード
ord-fe2b0d2769fe4845afe144cd2eb07c41
出典データセット
uspto-grants-2012_01
特許番号
US08097618B2

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