2(R)-(4-methoxybenzyl)-3-(piperidinocarbonyl)propionic acid → (2R, 4S, 5S)-N-Butyl-6-cyclohexyl-4-hydroxy-5-{N-[2(R)-(4-methoxybenzyl)-3-(piperidinocarbonyl)propionyl]-3-(4-thiazolyl)-L-alanyl}amino-2-methylhexanamide

HRID 1768838Notes

Reaction equation

HRID 1768838 reaction equation
C(OC([NH:8][C@H:9]([C:16]([NH:18][C@@H:19]([CH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[C@@H:20]([OH:31])[CH2:21][C@@H:22]([CH3:30])[C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:24])=[O:17])[CH2:10][C:11]1[N:12]=[CH:13][S:14][CH:15]=1)=O)(C)(C)C.[CH3:39][O:40][C:41]1[CH:60]=[CH:59][C:44]([CH2:45][C@H:46]([CH2:50][C:51]([N:53]2[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]2)=[O:52])[C:47]([OH:49])=O)=[CH:43][CH:42]=1>>[CH2:26]([NH:25][C:23](=[O:24])[C@H:22]([CH3:30])[CH2:21][C@H:20]([OH:31])[C@@H:19]([NH:18][C:16](=[O:17])[C@H:9]([CH2:10][C:11]1[N:12]=[CH:13][S:14][CH:15]=1)[NH:8][C:47](=[O:49])[C@H:46]([CH2:45][C:44]1[CH:43]=[CH:42][C:41]([O:40][CH3:39])=[CH:60][CH:59]=1)[CH2:50][C:51]([N:53]1[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]1)=[O:52])[CH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[CH2:27][CH2:28][CH3:29]

Participants

3

Reactant 2

HCID 150457582(R)-(4-methoxybenzyl)-3-(piperidinocarbonyl)propionic acidHCID 15045764(2R, 4S, 5S)-5-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-N-butyl-6-cyclohexyl-4-hydroxy-2-methylhexanamide

Product 1

HCID 15045740(2R, 4S, 5S)-N-Butyl-6-cyclohexyl-4-hydroxy-5-{N-[2(R)-(4-methoxybenzyl)-3-(piperidinocarbonyl)propionyl]-3-(4-thiazolyl)-L-alanyl}amino-2-methylhexanamideYield 23.5%

Procedure

The procedure described in Example 6(b) was repeated, but using 150 mg (0.27 mmole) of (2R, 4S, 5S)-5-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-N-butyl-6-cyclohexyl-4-hydroxy-2-methylhexanamide [prepared as described in Example 6(a)] and 86 mg (0.28 mmole) of 2(R)-(4-methoxybenzyl)-3-(piperidinocarbonyl)propionic acid, to afford 47 mg of the title compound as a white powder, melting at 120°-122° C.

Sources & evidence

ORD record
ord-c9eb1adcd4734871b7cb2e626f187e38
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

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