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-N-ethyl-4-hydroxy-2-methylhexanamide

HRID 1768843Notes

Reaction equation

HRID 1768843 reaction equation
C(OC([NH:8][C@H:9]([C:16]([NH:18][C@@H:19]([CH2:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[C@@H:20]([OH:29])[CH2:21][C@@H:22]([CH3:28])[C:23]([NH:25][CH2:26][CH3:27])=[O:24])=[O:17])[CH2:10][C:11]1[N:12]=[CH:13][S:14][CH:15]=1)=O)(C)(C)C.[CH2:37]([C@H:44]([CH2:48][C:49]([N:51]([CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[CH3:52])=[O:50])[C:45]([OH:47])=O)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[CH2:37]([C@H:44]([CH2:48][C:49]([N:51]([CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[CH3:52])=[O:50])[C:45]([NH:8][C@H:9]([C:16]([NH:18][C@@H:19]([CH2:30][CH:31]1[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1)[C@@H:20]([OH:29])[CH2:21][C@@H:22]([CH3:28])[C:23]([NH:25][CH2:26][CH3:27])=[O:24])=[O:17])[CH2:10][C:11]1[N:12]=[CH:13][S:14][CH:15]=1)=[O:47])[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

3

Reactant 2

HCID 150457542(R)-benzyl-3-(N-benzyl-N-methylaminocarbonyl)propionic acidHCID 15045769(2R, 4S, 5S)-5-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-N-ethyl-4-hydroxy-2-methylhexanamide

Product 1

HCID 15045746(2R, 4S, 5S)-5-{N-[2(R)-Benzyl-3-(N-benzyl-N-methylaminocarbonyl)propionyl]-3-(4-thiazolyl)-L-alanyl}amino-6-cyclohexyl-N-ethyl-4-hydroxy-2-methylhexanamideYield 29%

Procedure

The procedure described in Example 6(b) was repeated, but using 325 mg (0.62 mmole) of (2R, 4S, 5S)-5-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-N-ethyl-4-hydroxy-2-methylhexanamide [prepared as described in Example 19(a)] and 200 mg (0.64 mmole) of 2(R)-benzyl-3-(N-benzyl-N-methylaminocarbonyl)propionic acid, to afford 129 mg of the title compound as white crystals, melting at 148°-150° C.

Sources & evidence

ORD record
ord-6df18e238ae6445684d6a915b41d3dda
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

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