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

HRID 421229

반응식

HRID 421229 반응식
[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

참가 물질

7

반응물 4

HCID 81531Diisopropylethylamine2회HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11182647Methyl D-alaninate hydrochlorideHCID 112559791,4-Di-Boc-piperazine-2-carboxylic acid

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-fe2b0d2769fe4845afe144cd2eb07c41
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097618B2

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