(R)-3,3-Dimethyl-2-aminobutane → (+)-(R)-4-[3,4-dioxo-2-(1,2,2-trimethyl-propylamino)-cyclobut-1-enylamino]-3-ethylbenzonitrile

HRID 260800

반응식

HRID 260800 반응식
C(O[C:4]1[C:7](=[O:8])[C:6](=[O:9])[C:5]=1[NH:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[CH2:19][CH3:20])C.[CH3:21][C@@H:22]([NH2:27])[C:23]([CH3:26])([CH3:25])[CH3:24]>C(O)C>[O:8]=[C:7]1[C:6](=[O:9])[C:5]([NH:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=2[CH2:19][CH3:20])=[C:4]1[NH:27][C@H:22]([CH3:21])[C:23]([CH3:26])([CH3:25])[CH3:24]

참가 물질

4

반응물 2

HCID 5324845(R)-3,3-Dimethyl-2-aminobutaneHCID 199729184-(2-Ethoxy-3,4-dioxo-cyclobut-1-enylamino)-3-ethylbenzonitrile

생성물 1

HCID 9883778(+)-(R)-4-[3,4-dioxo-2-(1,2,2-trimethyl-propylamino)-cyclobut-1-enylamino]-3-ethylbenzonitrile수율 52.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

4-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-3-ethylbenzonitrile (1.26 g, 4.66 mmol) and a solution of (R)-1,2,2-trimethylpropylamine (9.3 mmol) in ethanol (58 mL) were stirred at room temperature for 24 hours. The resulting yellow solution was concentrated to a yellow oil, which was dissolved in acetonitrile (20 mL) and stirred at room temperature. The yellow solid which precipitated was filtered off and rinsed with ethyl acetate to yield 0.79 g (52%) of (+)-(R)-4-[3,4-dioxo-2-(1,2,2-trimethyl-propylamino)-cyclobut-1-enylamino]-3-ethylbenzonitrile as an off-white solid: mp 235°-237° C.; [α]D25 =+68.20° (DMSO, c 0.0072); 1H NMR (DMSO-d6): δ 8.04 (br s, 1H), 8.04 (d, 1H), 7.69-7.57 (m, 3H), 4.05 (m, 1H), 2.71 (q, 2H), 1.27-1.16 (overlapping doublet and triplet, 6H), 0.91 (s, 9H). IR (KBr): 3278, 2959, 2222, 1793, 1674, 1598, 1576, 1522 cm-1 ; MS (m/z) 325 (M+).

후처리

  1. concentrationThe resulting yellow solution was concentrated to a yellow oil, which
  2. dissolutionwas dissolved in acetonitrile (20 mL)
  3. customThe yellow solid which precipitated
  4. filtrationwas filtered off
  5. washrinsed with ethyl acetate

출처 및 근거

ORD 기록
ord-f065e4551d7d4e8ca1fab6f1c141b5c0
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05530025

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