(2R, 4S, 5S)-5-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-N-butyl-6-cyclohexyl-4-hydroxy-2-methylhexanamide → (2R, 4S, 5S)-N-Butyl-6-cyclohexyl-4-hydroxy-5-{N-[2(R)-(4-methoxybenzyl)-3-(N-benzyl-N-methylaminocarbonyl)-propionyl]-3-(4-thiazolyl)-L-alanyl}amino-2-methylhexanamide

HRID 1768837Notes

Reaction equation

HRID 1768837 reaction equation
C(O[C:6]([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:7])(C)(C)C.[CH3:39][O:40][C:41]1[CH:63]=[CH:62][C:44]([CH2:45][C@H:46]([CH2:50][C:51]([N:53]([CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH3:54])=[O:52])C(O)=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:6](=[O:7])[C@H:46]([CH2:45][C:44]1[CH:62]=[CH:63][C:41]([O:40][CH3:39])=[CH:42][CH:43]=1)[CH2:50][C:51]([N:53]([CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[CH3:54])=[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 15045764(2R, 4S, 5S)-5-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-N-butyl-6-cyclohexyl-4-hydroxy-2-methylhexanamideHCID 150457722(R)-(4-methoxybenzyl)-3-(N-benzyl-N-methylaminocarbonyl)propionic acid

Product 1

HCID 15045738(2R, 4S, 5S)-N-Butyl-6-cyclohexyl-4-hydroxy-5-{N-[2(R)-(4-methoxybenzyl)-3-(N-benzyl-N-methylaminocarbonyl)-propionyl]-3-(4-thiazolyl)-L-alanyl}amino-2-methylhexanamideYield 69.7%

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 92 mg (0.27 mmole) of 2(R)-(4-methoxybenzyl)-3-(N-benzyl-N-methylaminocarbonyl)propionic acid, to afford 146 mg of the title compound as a white powder, melting at 112°-114° C.

Sources & evidence

ORD record
ord-077b9972811b48f7a6b37d725b86859e
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

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