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-N-isobutyl-2-methylhexanamide

HRID 1768840Notes

Reaction equation

HRID 1768840 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][CH:27]([CH3:29])[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.[CH2:39]([C@H:46]([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])C(O)=O)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>>[CH2:39]([C@H:46]([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])[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][CH:27]([CH3:28])[CH3:29])=[O:24])=[O:17])[CH2:10][C:11]1[N:12]=[CH:13][S:14][CH:15]=1)=[O:7])[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

3

Reactant 2

HCID 150457542(R)-benzyl-3-(N-benzyl-N-methylaminocarbonyl)propionic acidHCID 15045767(2R, 4S, 5S)-5-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-4-hydroxy-N-isobutyl-2-methylhexanamide

Product 1

HCID 15045744(2R, 4S, 5S)-5-{N-[2(R)-Benzyl-3-(N-benzyl-N-methylaminocarbonyl)propionyl]-3-(4-thiazolyl)-L-alanyl}amino-6-cyclohexyl-4-hydroxy-N-isobutyl-2-methylhexanamideYield 53.3%

Procedure

The procedure described in Example 6(b) was repeated, but using 300 mg (0.543 mmole) of (2R, 4S, 5S)-5-[N-(t-butoxycarbonyl)-3-(4-thiazolyl)-L-alanyl]amino-6-cyclohexyl-4-hydroxy-N-isobutyl-2-methylhexanamide [prepared as described in Example 17(a)] and 170 mg (0.543 mmole) of 2(R)-benzyl-3-(N-benzyl-N-methylaminocarbonyl)propionic acid, to afford 216 mg of the title compound as a colorless powder, melting at 118°-120° C.

Sources & evidence

ORD record
ord-642d4d17c3d24b8e913a49816890efa5
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

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