t-butyl (S)-2-[[(R)-alpha-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]acetyl]-1-pyrrolidinecarboxylate → t-butyl (S)-2-[[(R)-alpha-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropylhexyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]-acetyl]-1-pyrrolidinecarboxylate

HRID 1655730Notes

Reaction equation

HRID 1655730 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:18][C:19]([C@@H:21]([NH:28][C:29]([C@H:31]([CH2:39][C:40]([C@@H:42]2[CH2:46][CH2:45][CH2:44][N:43]2[C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])=[O:41])[CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[CH2:22][C:23]2[N:24]=[CH:25][NH:26][CH:27]=2)=[O:20])[C@@H:9]([OH:17])[CH2:10][C@@H:11]([CH:14]([CH3:16])[CH3:15])[CH:12]=[CH2:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:54]1([CH2:60][C@H:61]([NH:71][C:72]([C@@H:74]([NH:81][C:82]([C@@H:84]([CH2:92][C:93]([C@@H:95]2[CH2:99][CH2:98][CH2:97][N:96]2[C:100]([O:102][C:103]([CH3:106])([CH3:105])[CH3:104])=[O:101])=[O:94])[CH2:85][C:86]2[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=2)=[O:83])[CH2:75][C:76]2[N:77]=[CH:78][NH:79][CH:80]=2)=[O:73])[C@@H:62]([OH:70])[CH2:63][C@@H:64]([CH:67]([CH3:69])[CH3:68])[CH:65]=[CH2:66])[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]1>>[CH:1]1([CH2:7][C@H:8]([NH:18][C:19]([C@@H:21]([NH:28][C:29]([C@H:31]([CH2:39][C:40]([C@@H:42]2[CH2:46][CH2:45][CH2:44][N:43]2[C:47]([O:49][C:50]([CH3:53])([CH3:51])[CH3:52])=[O:48])=[O:41])[CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[CH2:22][C:23]2[N:24]=[CH:25][NH:26][CH:27]=2)=[O:20])[C@@H:9]([OH:17])[CH2:10][C@@H:11]([CH:14]([CH3:15])[CH3:16])[CH2:12][CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:54]1([CH2:60][C@H:61]([NH:71][C:72]([C@@H:74]([NH:81][C:82]([C@@H:84]([CH2:92][C:93]([C@@H:95]2[CH2:99][CH2:98][CH2:97][N:96]2[C:100]([O:102][C:103]([CH3:106])([CH3:104])[CH3:105])=[O:101])=[O:94])[CH2:85][C:86]2[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=2)=[O:83])[CH2:75][C:76]2[N:77]=[CH:78][NH:79][CH:80]=2)=[O:73])[C@@H:62]([OH:70])[CH2:63][C@@H:64]([CH:67]([CH3:68])[CH3:69])[CH2:65][CH3:66])[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]1

Participants

4

Reactant 2

HCID 178456009t-butyl (S)-2-[[(R)-alpha-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]acetyl]-1-pyrrolidinecarboxylateHCID 178456010HCID 178456010, compound

Product 2

HCID 178456011t-butyl (S)-2-[[(R)-alpha-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropylhexyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]-acetyl]-1-pyrrolidinecarboxylateHCID 178456012t-butyl (S)-2-[[(S)-alpha-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropylhexyl]carbamoyl]-2-imidazol-4-ylethyl]-carbamoyl]phenethyl]acetyl]-1-pyrrolidinecarboxylate

Procedure

In a manner analogous to that described in Example 2, by catalytically hydrogenating t-butyl (S)-2-[[(S)-α-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]carbamoyl]-2-imidazol-4-ylethyl]-carbamoyl]-phenethyl]acetyl]-1-pyrrolidinecarboxylate and t-butyl (S)-2-[[(R)-α-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]acetyl]-1-pyrrolidinecarboxylate, there was obtained t-butyl (S)-2-[[(S)-α-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropylhexyl]carbamoyl]-2-imidazol-4-ylethyl]-carbamoyl]phenethyl]acetyl]-1-pyrrolidinecarboxylate (less polar isomer) and t-butyl (S)-2-[[(R)-α-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropylhexyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]-acetyl]-1-pyrrolidinecarboxylate. MS: 736 (M+H)+

Sources & evidence

ORD record
ord-aef909e7bd2c4fec86af75cff58f12a3
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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