(2R,5R)-2,5-dibenzyl-6-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-ylamino)-6-oxohexanoic acid → (2R,5R)-2,5-Dibenzyl-N1-((4S,7R,10aS)-7-ethyl-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-N6-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-yl)hexanediamide

HRID 529625Notes

Reaction equation

HRID 529625 reaction equation
[CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:15]([NH:17][C@H:18]1[CH2:24][CH2:23][CH2:22][CH2:21][N:20]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])[C:19]1=[O:33])=[O:16])[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.[NH2:48][CH:49]1[CH2:55][CH2:54][S:53][CH:52]2[CH2:56][CH2:57][CH2:58][CH:59]([CH2:60][CH3:61])[N:51]2[C:50]1=[O:62]>>[CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:15]([NH:17][C@H:18]1[CH2:24][CH2:23][CH2:22][CH2:21][N:20]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])[C:19]1=[O:33])=[O:16])[C:9]([NH:48][C@H:49]1[CH2:55][CH2:54][S:53][C@H:52]2[CH2:56][CH2:57][CH2:58][C@@H:59]([CH2:60][CH3:61])[N:51]2[C:50]1=[O:62])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 68310532(2R,5R)-2,5-dibenzyl-6-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-ylamino)-6-oxohexanoic acidHCID 867062594-Amino-7-ethylhexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one trifluoroacetate

Product 1

HCID 68311201(2R,5R)-2,5-Dibenzyl-N1-((4S,7R,10aS)-7-ethyl-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-N6-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-yl)hexanediamide

Procedure

(2R,5R)-2,5-Dibenzyl-N1-((4S,7R,10aS)-7-ethyl-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-N6-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-yl)hexanediamide was synthesized as described in General Procedure H using Intermediate 70 (36 mg, 0.067 mmol) and Intermediate 74 (23 mg, 0.067 mmol) to give a white solid (25 mg, 49% yield). Anal. Calcd. for C44H56N4O5S m/z 752.7. found: 753.6 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.41-7.07 (m, 11H), 7.07-6.87 (m, 3H), 5.24 (s, 1H), 5.00-4.84 (m, 1H), 4.81-4.69 (m, 1H), 4.38-4.26 (m, 1H), 4.09-3.83 (m, 1H), 3.79 (d, J=3.5 Hz, 3H), 3.47-3.27 (m, 1H), 3.22-3.03 (m, 1H), 2.90-2.54 (m, 5H), 2.45-2.28 (m, 2H), 2.23-1.94 (m, 11H), 1.93-1.76 (m, 3H), 1.77-1.59 (m, 4H), 1.50 (d, J=29.0 Hz, 3H), 1.39-1.22 (m, 1H), 0.97-0.82 (m, 3H).

Sources & evidence

ORD record
ord-eb47f6e9928c45769652be1645a578b3
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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