Dicyclohexylcarbodiimide → HCID 67353472, 화합물

HRID 75853노트

반응식

HRID 75853 반응식
[OH:1][C@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=O.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:23]=[C:22]([C:24]([NH:26][CH:27]([CH:32]([CH3:34])[CH3:33])[C:28]([O:30][CH3:31])=[O:29])=[O:25])[O:21][N:20]=2)=[CH:15][CH:14]=1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>>[OH:1][C@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:23]=[C:22]([C:24]([NH:26][CH:27]([CH:32]([CH3:34])[CH3:33])[C:28]([O:30][CH3:31])=[O:29])=[O:25])[O:21][N:20]=2)=[CH:15][CH:14]=1)=[O:5]

참가 물질

5

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 11914(-)-Mandelic acidHCID 757711-HydroxybenzotriazoleHCID 67352790Methyl 2-(3-(4-aminophenyl)isoxazole-5-carboxamido)-3-methylbutanoate

생성물 1

HCID 67353472HCID 67353472, 화합물수율 39.6%

실험 절차

To (R)-2-hydroxy-2-phenylacetic acid (200 mg), methyl 2-(3-(4-aminophenyl) isoxazole-5-carboxamido)-3-methylbutanoate (417 mg), in N,N′-Dimethyl formamide (5 ml), DCC (406 mg) and HOBT (177 mg) were added and stirred at RT for 16 hours. The reaction mixture was filtered and concentrated to obtain brown oil which was purified by column chromatography (silica gel, EtOAc—CHCl3) to obtain pale brown solid which was crystallized from DCM-Petroleum ether to yield 235 mg (39%) of the title compound as off white solid. MS (ES+): m/z 452 (M+1); 1H NMR (DMSO-d6; 300 MHz): δ 10.19 (s, 1H), 9.2 (d, 1H), 7.88 (d, 4H), 7.69 (s, 1H), 7.54 (m, 2H), 7.39-7.27 (m, 3H), 6.51 (d, 1H), 5.13 (d, 1H), 4.3 (m, 1H), 3.67 (s, 3H), 2.24 (m, 1H), 0.96 (d, 6H).

후처리

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customto obtain brown oil which
  4. customwas purified by column chromatography (silica gel, EtOAc—CHCl3)
  5. customto obtain pale brown solid which
  6. customwas crystallized from DCM-Petroleum ether

출처 및 근거

ORD 기록
ord-3bdc70ef764a44cd916f066b9e0c2012
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835428B2

반응 노트

불러오는 중…