2(R)-(4-Methoxybenzyl)-3-(morpholinocarbonyl)propionic acid → (2S, 4S, 5S)-5-{N-[2(R)-(4-Methoxybenzyl)-3-(morpholinocarbonyl)propionyl]-3-(4-thiazolyl)-L-alanyl}amino-6-cyclohexyl-4-hydroxy-2-isopropyl-N-methylhexanamid

HRID 1768832Notes

Reaction equation

HRID 1768832 reaction equation
C(O[C:6]([NH:8][C@H:9]([C:16]([NH:18][C@@H:19]([CH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[C@@H:20]([OH:30])[CH2:21][C@@H:22]([CH:27]([CH3:29])[CH3:28])[C:23]([NH:25][CH3:26])=[O:24])=[O:17])[CH2:10][C:11]1[N:12]=[CH:13][S:14][CH:15]=1)=[O:7])(C)(C)C.[CH3:38][O:39][C:40]1[CH:59]=[CH:58][C:43]([CH2:44][C@H:45]([CH2:49][C:50]([N:52]2[CH2:57][CH2:56][O:55][CH2:54][CH2:53]2)=[O:51])C(O)=O)=[CH:42][CH:41]=1>>[CH3:38][O:39][C:40]1[CH:41]=[CH:42][C:43]([CH2:44][C@H:45]([CH2:49][C:50]([N:52]2[CH2:57][CH2:56][O:55][CH2:54][CH2:53]2)=[O:51])[C:6]([NH:8][C@H:9]([C:16]([NH:18][C@@H:19]([CH2:31][CH:32]2[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]2)[C@@H:20]([OH:30])[CH2:21][C@@H:22]([CH:27]([CH3:29])[CH3:28])[C:23]([NH:25][CH3:26])=[O:24])=[O:17])[CH2:10][C:11]2[N:12]=[CH:13][S:14][CH:15]=2)=[O:7])=[CH:58][CH:59]=1

Participants

3

Reactant 2

HCID 144294732(R)-(4-Methoxybenzyl)-3-(morpholinocarbonyl)propionic acidHCID 15045729(2S, 4S, 5S)-5-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-4-hydroxy-2-isopropyl-N-methylhexanamide

Product 1

HCID 15045732(2S, 4S, 5S)-5-{N-[2(R)-(4-Methoxybenzyl)-3-(morpholinocarbonyl)propionyl]-3-(4-thiazolyl)-L-alanyl}amino-6-cyclohexyl-4-hydroxy-2-isopropyl-N-methylhexanamidYield 70%

Procedure

The procedure described in Example 1(b) was repeated, but using 200 mg (0.37 mmole) of (2S, 4S, 5S)-5-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-4-hydroxy-2-isopropyl-N-methylhexanamide [prepared as described in Example 1(a)] and 137 mg (0.45 mmole) of 2(R)-(4-methoxybenzyl)-3-(morpholinocarbonyl)propionic acid, to afford 188 mg (yield 70%) of the title compound as white crystals, melting at 128°-130° C.

Sources & evidence

ORD record
ord-6be9e0443c104ed3b8ec47bc2a36ce44
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

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