DL-cysteine → 2-(7-(3-Cyano-4-isopropoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid

HRID 515667

반응식

HRID 515667 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[O:31][CH:32]([CH3:34])[CH3:33])[CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:14]2[N:13]3[CH2:17][CH2:18][CH:19]([CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])[C:12]3=[CH:11][C:10]=2[CH:9]=1)#[N:2].NC(CS)C(O)=O>C(O)(C(F)(F)F)=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[O:31][CH:32]([CH3:34])[CH3:33])[CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:14]2[N:13]3[CH2:17][CH2:18][CH:19]([CH2:20][C:21]([OH:23])=[O:22])[C:12]3=[CH:11][C:10]=2[CH:9]=1)#[N:2]

참가 물질

4

반응물 2

HCID 594DL-cysteineHCID 67252091tert-Butyl 2-(7-(3-cyano-4-isopropoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

생성물 1

HCID 672491622-(7-(3-Cyano-4-isopropoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid수율 86.2%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

tert-Butyl 2-(7-(3-cyano-4-isopropoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (452 mg, 0.981 mmol) was added to a solution of 2-amino-3-mercaptopropanoic acid (214 mg, 1.767 mmol) in TFA (5 mL) and was stirred at room temperature for 15 min. The reaction mixture was poured into ice water. The white precipitate was collected by filtration to provide the title compound (342 mg). LCMS m/z=405.5 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.40 (d, J=6.1 Hz, 6H), 2.26-2.36 (m, 1H), 2.66 (dd, J=16.4, 8.5 Hz, 1H), 2.85-2.97 (m, 2H), 3.72-3.80 (m, 1H), 3.98-4.06 (m, 1H), 4.10-4.17 (m, 1H), 4.65 (septet, J=6.1 Hz, 1H), 5.00 (s, 2H), 6.12 (s, 1H), 6.84 (dd, J=8.8, 2.4 Hz, 1H), 6.96 (d, J=8.7 Hz, 1H), 7.06 (d, J=2.4 Hz, 1H), 7.14 (d, J=8.7 Hz, 1H), 7.58 (dd, J=8.8, 2.4 Hz, 1H), 7.64 (d, J=2.1 Hz, 1H).

후처리

  1. filtrationThe white precipitate was collected by filtration

출처 및 근거

ORD 기록
ord-b1aa06c0cc4c46798bb3d1bc9f93245c
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108969B2

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