Leucine, N-carboxy-, N-benzyl ester, L- → (2S)-2-(benzyloxycarbonyl)amino-N-(4-carboethoxythiazol-2-yl)methyl-4-methylpentanamide

HRID 412084Notes

Reaction equation

HRID 412084 reaction equation
C(O[C:6]([NH:8][C@H:9]([C:14]1[S:15][CH:16]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:18]=1)CC(C)C)=[O:7])(C)(C)C.[C:24]([NH:34][C@H:35](C(O)=O)[CH2:36][CH:37]([CH3:39])[CH3:38])([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25].C(N[C@H](C(N[C@H](C(O)=O)CC(C)C)=O)CC(C)C)(OCC1C=CC=CC=1)=O>>[CH2:27]([O:26][C:24]([NH:34][C@@H:35]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:6]([NH:8][CH2:9][C:14]1[S:15][CH:16]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:18]=1)=[O:7])=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 3

HCID 74840Leucine, N-carboxy-, N-benzyl ester, L-HCID 7299379N-((Phenylmethoxy)carbonyl)-L-leucyl-L-leucineHCID 14680168(1S)1-(tert-butoxycarbonyl)amino-1-(4carboethoxythiazol-2-yl)-3-methylbutane

Product 1

HCID 18396119(2S)-2-(benzyloxycarbonyl)amino-N-(4-carboethoxythiazol-2-yl)methyl-4-methylpentanamide

Procedure

Following the procedure of Example 13, except substituting 1-(tert-butoxycarbonyl)amino-1-(4-carboethoxythiazol-2-yl)methane for (1S)-1-(tert-butoxycarbonyl)amino-1-(4-carboethoxythiazol-2-yl)-3-methylbutane, and N-Cbz-L-leucine for N-Cbz-L-leucinyl-L-leucine, the title compound was prepared (0.120 g, 32%). MS (MH+): 434.2.

Sources & evidence

ORD record
ord-e0f537e21cc24b549be60d9507fb8c69
Source dataset
uspto-grants-2003_05
Patent number
US06562842B2

Reaction notes

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