2(R)-benzyl-3-(N-benzyl-N-methylaminocarbonyl)propionic acid → (2R, 4S, 5S)-5-{N-[2(R)-Benzyl-3-(N-benzyl-N-methylaminocarbonyl)propionyl]-3-(4-thiazolyl)-L-alanyl}amino-6-cyclohexyl-4-hydroxy-2-methyl-N-propylhexanamide

HRID 1768842Notes

Reaction equation

HRID 1768842 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]([CH3:29])[C:23]([NH:25][CH2:26][CH2:27][CH3:28])=[O:24])=[O:17])[CH2:10][C:11]1[N:12]=[CH:13][S:14][CH:15]=1)=[O:7])(C)(C)C.[CH2:38]([C@H:45]([CH2:49][C:50]([N:52]([CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[CH3:53])=[O:51])C(O)=O)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>>[CH2:38]([C@H:45]([CH2:49][C:50]([N:52]([CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[CH3:53])=[O:51])[C:6]([NH:8][C@H:9]([C:16]([NH:18][C@@H:19]([CH2:31][CH:32]1[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1)[C@@H:20]([OH:30])[CH2:21][C@@H:22]([CH3:29])[C:23]([NH:25][CH2:26][CH2:27][CH3:28])=[O:24])=[O:17])[CH2:10][C:11]1[N:12]=[CH:13][S:14][CH:15]=1)=[O:7])[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

3

Reactant 2

HCID 150457542(R)-benzyl-3-(N-benzyl-N-methylaminocarbonyl)propionic acidHCID 15045768(2R, 4S, 5S)-5-[N-(t-Butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-4-hydroxy-2-methyl-N-propylhexanamide

Product 1

HCID 15045745(2R, 4S, 5S)-5-{N-[2(R)-Benzyl-3-(N-benzyl-N-methylaminocarbonyl)propionyl]-3-(4-thiazolyl)-L-alanyl}amino-6-cyclohexyl-4-hydroxy-2-methyl-N-propylhexanamideYield 32.4%

Procedure

The procedure described in Example 6(b) was repeated, but using 252 mg (0.468 mmole) of (2R, 4S, 5S)-5-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-4-hydroxy-2-methyl-N-propylhexanamide [prepared as described in Example 18(a)] and 152 mg (0.488 mmole) of 2(R)-benzyl-3-(N-benzyl-N-methylaminocarbonyl)propionic acid, to afford 111 mg of the title compound as a colorless powder, melting at 115°-118° C.

Sources & evidence

ORD record
ord-00122406129940e8ae918264aaeecf03
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

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