Amantadine → HCID 57978236, compound

HRID 1866558Notes

Reaction equation

HRID 1866558 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[CH2:16][NH:17][C:18]([CH3:31])([CH3:30])[CH2:19][C:20]2[CH:21]=[C:22]([CH2:26][C:27](O)=[O:28])[CH:23]=[CH:24][CH:25]=2)=[CH:11][C:10]=1[CH2:40][OH:41])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:42]12([NH2:52])[CH2:51][CH:46]3[CH2:47][CH:48]([CH2:50][CH:44]([CH2:45]3)[CH2:43]1)[CH2:49]2>>[C:42]12([NH:52][C:27](=[O:28])[CH2:26][C:22]3[CH:23]=[CH:24][CH:25]=[C:20]([CH2:19][C:18]([NH:17][CH2:16][C@@H:15]([C:12]4[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)=[C:10]([CH2:40][OH:41])[CH:11]=4)[O:32][Si:33]([C:36]([CH3:37])([CH3:39])[CH3:38])([CH3:35])[CH3:34])([CH3:31])[CH3:30])[CH:21]=3)[CH2:49][CH:48]3[CH2:47][CH:46]([CH2:45][CH:44]([CH2:50]3)[CH2:43]1)[CH2:51]2

Participants

3

Reactant 2

HCID 2130AmantadineHCID 57978223HCID 57978223, compound

Product 1

HCID 57978236HCID 57978236, compoundYield 71%

Procedure

The title compound was prepared from (3-{2-[((2R)-2-[4-(benzyloxy)-3-(hydroxymethyl)phenyl]-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]-2-methyl propyl}phenyl)acetic acid (preparation 148) and 1-adamantylamine, using a similar method to that of preparation 38, as a yellow oil in 71% yield. 1H NMR (400 MHz, DMSO-d6) δ: 7.52 (3H, m), 7.52-7.24 (4H, m), 7.18-7.08 (2H, m), 7.07-6.98 (2H, m), 6.94 (1H, m), 5.09 (2H, d), 5.01 (1H, t), 4.66-4.61 (1H, m), 4.54 (2H, d), 3.25 (2H, d), 3.15 (1H, d), 2.59-2.43 (2H, m), 1.98-1.92 (3H, m), 1.87 (6H, m), 1.57 (6H, m), 0.96 (6H, dd), 0.79 (9H, d), -0.98 (3H, s), -0.93 (3H, s) ppm; LRMS ESI m/z 712 [M+H]+

Workup

  1. customof preparation 38

Sources & evidence

ORD record
ord-c5ca6882c59b4046a8c5c5dc4669d198
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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