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

HRID 1768839Notes

Reaction equation

HRID 1768839 reaction equation
C(OC([NH:8][C@H:9]([C:16]([NH:18][C@@H:19]([CH2:34][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[C@@H:20]([OH:33])[CH2:21][C@@H:22]([CH:30]([CH3:32])[CH3:31])[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.[CH2:41]([C@H:48]([CH2:52][C:53]([N:55]([CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[CH3:56])=[O:54])[C:49]([OH:51])=O)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>>[CH2:41]([C@H:48]([CH2:52][C:53]([N:55]([CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[CH3:56])=[O:54])[C:49]([NH:8][C@H:9]([C:16]([NH:18][C@@H:19]([CH2:34][CH:35]1[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1)[C@@H:20]([OH:33])[CH2:21][C@@H:22]([CH:30]([CH3:31])[CH3:32])[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:51])[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

3

Reactant 2

HCID 150457542(R)-benzyl-3-(N-benzyl-N-methylaminocarbonyl)propionic acidHCID 15045763(2S, 4S, 5S)-5-[N-(t-Butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-N-butyl-6-cyclohexyl-4-hydroxy-2-isopropylhexanamide

Product 1

HCID 15045743(2S, 4S, 5S)-5-{N-[2(R)-Benzyl-3-(N-benzyl-N-methylaminocarbonyl)propionyl]-3-(4-thiazolyl)-L-alanyl}amino-N-butyl-6-cyclohexyl-4-hydroxy-2-isopropylhexanamideYield 50.3%

Procedure

The procedure described in Example 2(b) was repeated, but using 280 mg (0.48 mmole) of (2S, 4S, 5S)-5-[N-(t-butoxycarbonyl)-3-(4-thiazolyl )-L-alanyl]amino-N-butyl-6-cyclohexyl-4-hydroxy-2-isopropylhexanamide [prepared as described in Example 2(a)] and 150 mg (0.48 mmole) of 2(R)-benzyl-3-(N-benzyl-N-methylaminocarbonyl)propionic acid, to afford 187 mg of the title compound as a white powder, melting at 155°-156° C.

Sources & evidence

ORD record
ord-dbeedbe0e72948b48dbe5897ba8ffd74
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

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