N-Cbz-d-alanine → HCID 178462188, compound

HRID 2294741Notes

Reaction equation

HRID 2294741 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:14]([OH:16])=O)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]1([CH2:23][C@H:24]([NH:32][C:33](=[O:53])[C@@H:34]([NH:41][C:42](=[O:52])[C@H:43]([CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[NH2:44])[CH2:35][C:36]2[N:37]=[CH:38][NH:39][CH:40]=2)[C@@H:25]([OH:31])[C@H:26]([CH:28]2[CH2:30][CH2:29]2)[OH:27])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>>[CH:17]1([CH2:23][C@H:24]([NH:32][C:33]([C@@H:34]([NH:41][C:42]([C@@H:43]([NH:44][C:14]([C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH3:13])=[O:16])[CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:52])[CH2:35][C:36]2[N:37]=[CH:38][NH:39][CH:40]=2)=[O:53])[C@@H:25]([OH:31])[C@H:26]([CH:28]2[CH2:29][CH2:30]2)[OH:27])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 70832N-Cbz-d-alanineHCID 178511770HCID 178511770, compound

Product 1

HCID 178462188HCID 178462188, compound

Procedure

In an analogous manner to that described in Example 21, by replacing Boc-D-proline by N-benzyloxycarbonyl-D-alanine in the condensation with (S)-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-α-[(3-phenyl-L-alanyl)amino]imidazole-4-propionamide there was obtained benzyl [(R)-1-[[(S)-α-[[(S)-1-[[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]carbamoyl]ethyl]carbamate as an amorphous solid, MS: 717 (M+H)+.

Sources & evidence

ORD record
ord-fa256647d6de4f85b1e976fc2d23b649
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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