(2R,5R)-2,5-dibenzylhexanedioic acid → (2R,5R)-2,5-Dibenzyl-N1,N6-bis((4S,10aS)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)hexanediamide

HRID 529590Notes

Reaction equation

HRID 529590 reaction equation
C([C@@H]([CH2:12][CH2:13][C@H:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15](O)=[O:16])C(O)=O)C1C=CC=CC=1.[NH2:25][C@H:26]1[CH2:32][CH2:31][S:30][C@H:29]2[CH2:33][CH2:34][CH2:35][CH2:36][N:28]2[C:27]1=[O:37]>>[CH2:18]([C@@H:14]([CH2:13][CH2:12][C@H:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15]([NH:25][C@H:26]1[CH2:32][CH2:31][S:30][C@H:29]2[CH2:33][CH2:34][CH2:35][CH2:36][N:28]2[C:27]1=[O:37])=[O:16])[C:15]([NH:25][C@H:26]1[CH2:32][CH2:31][S:30][C@H:29]2[CH2:33][CH2:34][CH2:35][CH2:36][N:28]2[C:27]1=[O:37])=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 68292409(2R,5R)-2,5-dibenzylhexanedioic acidHCID 86706213(4S,10aS)-4-aminohexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one

Product 1

HCID 86706247(2R,5R)-2,5-Dibenzyl-N1,N6-bis((4S,10aS)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)hexanediamide

Procedure

(2R,5R)-2,5-Dibenzyl-N1,N6-bis((4S,10aS)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)hexanediamide was synthesized as described in General Procedure F using Intermediate 3 (20 mg, 0.061 mmol) and Intermediate 40 (29.5 mg, 0.147 mmol) to give a white solid (27 mg, 64% yield). Anal. Calcd. for C38H50N4O4S2 m/z 690.7. found: 691.5 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.32-7.05 (m, 10H), 6.86 (d, J=6.7 Hz, 2H), 5.28 (t, J=4.0 Hz, 2H), 5.04-4.91 (m, 2H), 4.23 (d, J=13.6 Hz, 2H), 3.12 (ddd, J=13.9, 11.0, 2.6 Hz, 1H), 3.02-2.87 (m, 2H), 2.81 (dd, J=13.4, 9.6 Hz, 2H), 2.71 (dd, J=13.3, 5.7 Hz, 2H), 2.58 (ddd, J=14.3, 6.0, 2.9 Hz, 2H), 2.43-2.31 (m, 2H), 2.11-1.75 (m, 9H), 1.76-1.60 (m, 4H), 1.60-1.38 (m, 6H), 1.33-1.18 (m, 2H).

Sources & evidence

ORD record
ord-dbe484f5f8604e5da04c3c3672030d14
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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