Piperidine → HCID 178451944, compound

HRID 2294716Notes

Reaction equation

HRID 2294716 reaction equation
N1CCCCC1.[CH:7]1([CH2:13][C@H:14]([NH:22][C:23](=[O:43])[C@@H:24]([NH:31][C:32](=[O:42])[C@H:33]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[NH2:34])[CH2:25][C:26]2[N:27]=[CH:28][NH:29][CH:30]=2)[C@@H:15]([OH:21])[C@H:16]([CH:18]2[CH2:20][CH2:19]2)[OH:17])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[N:44]1([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:51][CH2:50][CH2:49][C@@H:45]1[C:46](O)=[O:47]>C(Cl)Cl>[C:55]([O:54][C:52]([N:44]1[CH2:51][CH2:50][CH2:49][C@@H:45]1[C:46](=[O:47])[NH:34][C@H:33]([C:32](=[O:42])[NH:31][C@H:24]([C:23](=[O:43])[NH:22][C@@H:14]([CH2:13][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[C@@H:15]([OH:21])[C@H:16]([CH:18]1[CH2:19][CH2:20]1)[OH:17])[CH2:25][C:26]1[N:27]=[CH:28][NH:29][CH:30]=1)[CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:53])([CH3:58])([CH3:57])[CH3:56]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 178511770HCID 178511770, compound

Product 1

HCID 178451944HCID 178451944, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In an analogous manner to that described in Example 19, by condensing (S)-α-amino-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]imidazole-4-propionamide with Fmoc-Phe-OH there was obtained 9H-fluoren-9-ylmethyl [(S)-α-[[(S)-1-[[(1S,2R, 3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]carbamate which, by reaction with piperidine in methylene chloride, was converted into (S)-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-α-[(3-phenyl-L-alanyl)amino]imidazole-4-propionamide. Further condensation with Boc-D-Pro-OH, analogously to Example 19, yielded (R)-2-[[(S)-α-[[(S)-1-[[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]carbamoyl]-1-pyrrolidinecarboxylic acid tert-butyl ester as an amorphous solid, MS: 709 (M+H)+.

Sources & evidence

ORD record
ord-728bbabfb2074c04a5dadb21e5702e71
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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