N-((9H-Fluoren-9-ylmethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteine → (3R,9aS)-3-Aminohexahydropyrido[2,1-b][1,3]thiazin-4(6H)-one

HRID 529469

반응식

HRID 529469 반응식
[NH2:1][C@H:2]1[C:7](C)(C)[S:6][C@H:5]2[CH2:10][CH2:11][CH2:12][CH2:13][N:4]2[C:3]1=[O:14].C1C2C(COC(N[C@@H](CSC(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)C(O)=O)=O)C3C(=CC=CC=3)C=2C=CC=1>>[NH2:1][C@H:2]1[CH2:7][S:6][C@H:5]2[CH2:10][CH2:11][CH2:12][CH2:13][N:4]2[C:3]1=[O:14]

참가 물질

3

반응물 2

HCID 128239N-((9H-Fluoren-9-ylmethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteineHCID 68292898(3R,9aS)-3-Amino-2,2-dimethylhexahydropyrido[2,1-b][1,3]thiazin-4(6H)-one

생성물 1

HCID 68292198(3R,9aS)-3-Aminohexahydropyrido[2,1-b][1,3]thiazin-4(6H)-one

실험 절차

(3R,9aS)-3-Aminohexahydropyrido[2,1-b][1,3]thiazin-4(6H)-one (350 mg, 1.879 mmol) was synthesized as described for the preparation of Intermediate 30 using (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tritylthio)propanoic acid in step A. 1H NMR (500 MHz, CD3OD) δ ppm 4.66-4.58 (m, 1H), 4.51 (dd, J=11.55, 2.75 Hz, 1H), 4.20 (dd, J=11.27, 5.22 Hz, 1H), 3.28-3.22 (m, 1H), 3.01 (dd, J=13.20, 4.95 Hz, 1H), 2.81 (td, J=12.65, 2.75 Hz, 1H), 2.10-1.99 (m, 1H), 1.95 (d, J=7.15 Hz, 2H), 1.82-1.71 (m, 1H), 1.67 (d, J=13.75 Hz, 1H), 1.53-1.41 (m, 1H); 13C NMR (126 MHz, CD3OD) δ ppm 165.13, 60.06, 52.13, 47.02, 35.88, 25.73, 25.18, 24.71.

출처 및 근거

ORD 기록
ord-64016be9df9c4eaa946208a5286f900d
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346852B2

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