(4S,7S,10aS)-4-Amino-7-(1,3,4-oxadiazol-2-yl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one 2,2,2-trifluoroacetate → (2R,5R)-N1-((4S,7S,10aS)-7-(1,3,4-Oxadiazol-2-yl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-2,5-dibenzyl-N6-((S)-2-oxo-1-phenylazepan-3-yl)hexanediamide

HRID 529615Notes

Reaction equation

[CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:15](=[O:31])[NH:16][C@@H:17]1[CH2:23][CH2:22][CH2:21][CH2:20][N:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]1=[O:30])[C:9](O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[NH2:46][C@H:47]1[CH2:53][CH2:52][S:51][C@H:50]2[CH2:54][CH2:55][CH2:56][C@@H:57]([C:58]3[O:59][CH:60]=[N:61][N:62]=3)[N:49]2[C:48]1=[O:63]>>[O:59]1[CH:60]=[N:61][N:62]=[C:58]1[C@H:57]1[N:49]2[C@@H:50]([S:51][CH2:52][CH2:53][C@H:47]([NH:46][C:9](=[O:10])[C@@H:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:12][CH2:13][C@H:14]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:15]([NH:16][C@H:17]3[CH2:23][CH2:22][CH2:21][CH2:20][N:19]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:18]3=[O:30])=[O:31])[C:48]2=[O:63])[CH2:54][CH2:55][CH2:56]1

Participants

Reactant 2

HCID 68292026(4S,7S,10aS)-4-Amino-7-(1,3,4-oxadiazol-2-yl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one 2,2,2-trifluoroacetate

HCID 86706193(2R,5R)-2,5-dibenzyl-6-oxo-6-((R)-2-oxo-1-phenylazepan-3-ylamino)hexanoic acid

Product 1

HCID 66546462(2R,5R)-N1-((4S,7S,10aS)-7-(1,3,4-Oxadiazol-2-yl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-2,5-dibenzyl-N6-((S)-2-oxo-1-phenylazepan-3-yl)hexanediamide

Procedure

(2R,5R)—N1-((4S,7S,10aS)-7-(1,3,4-Oxadiazol-2-yl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-2,5-dibenzyl-N6-((S)-2-oxo-1-phenylazepan-3-yl)hexanediamide was synthesized as described in General Procedure H using Intermediate 24 (10 mg, 0.020 mmol) and Intermediate 35 (7.1 mg, 0.023 mmol) to give a white solid (3.5 mg, 24% yield). Anal. Calcd. for C43H50N6O5S m/z 762.7. found: 763.3 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 8.31 (1H, s), 7.40-7.32 (2H, m), 7.31-7.07 (13H, m), 7.02-6.90 (2H, m), 5.91 (1H, d, J=4.9 Hz), 5.27 (1H, t, J=4.4 Hz), 5.05-4.97 (1H, m), 4.78 (1H, dd, J=9.3, 6.6 Hz), 3.93 (1H, dd, J=15.1, 11.3 Hz), 3.59 (1H, dd, J=14.8, 4.9 Hz), 3.18-3.07 (1H, m), 2.90-2.68 (6H, m), 2.55 (1H, ddd, J=14.3, 5.5, 2.7 Hz), 2.46-2.33 (2H, m), 2.14-1.80 (8H, m), 1.77-1.65 (4H, m), 1.64-1.25 (4H, m).

Sources & evidence

ORD record: ord-1bc580add62b4a18bce692c5b1e34a03
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346852B2

Reaction notes

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