Diisopropylethylamine → ethyl (R) 3-[4-(2-{4-[(2,3-dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl}-acetylamino)-phenyl]-butyrate

HRID 1167809노트

반응식

HRID 1167809 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH3:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[N:16]1([C:25]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][C:35](O)=[O:36])=[CH:30][C:29]=2[O:38][CH3:39])=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[N:16]1([C:25]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][C:35]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([C@H:8]([CH3:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=3)=[O:36])=[CH:30][C:29]=2[O:38][CH3:39])=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17]1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 229942374-[(2,3-Dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl-acetic acidHCID 53963459HCID 53963459, 화합물

생성물 1

HCID 86585371ethyl (R) 3-[4-(2-{4-[(2,3-dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl}-acetylamino)-phenyl]-butyrate수율 86.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A solution of ethyl (R) 3-(4-aminophenyl)butyrate (790 mg), 4-[(2,3-dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl-acetic acid (1.24 g, Reference Example 5) and O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (1.45 g) in dimethylformamide (20 mL) was treated in one portion with diisopropylethylamine (1.4 mL). The resulting mixture was stirred at room temperature for 2 hours then poured into water (100 mL) and then extracted three times with ethyl acetate (50 mL). The combined extracts were washed with hydrochloric acid (0.5M), then with sodium hydrogen carbonate solution, then dried and then evaporated. The residue was triturated with a mixture of ethyl acetate and petrol to give the title compound (1.7 g) as a pink/orange powder. HPLC: RT=18.9 minutes (86% by ELS).

후처리

  1. extractionextracted three times with ethyl acetate (50 mL)
  2. washThe combined extracts were washed with hydrochloric acid (0.5M)
  3. dry with materialwith sodium hydrogen carbonate solution, then dried
  4. customevaporated
  5. customThe residue was triturated with a mixture of ethyl acetate and petrol

출처 및 근거

ORD 기록
ord-82ed5716f1d54d2993bb5518995d74e8
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06620832B2

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