Methane → (2S)-2-(benzyloxycarbonyl)amino-N-(4-carboethoxythiazol-2-yl)methyl-4-methylpentanamide

HRID 1356495Notes

Reaction equation

HRID 1356495 reaction equation
C.C(O[C:7]([NH:9][C@H:10]([C:15]1[S:16][CH:17]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:19]=1)CC(C)C)=[O:8])(C)(C)C.[C:25]([NH:35][C@H:36](C(O)=O)[CH2:37][CH:38]([CH3:40])[CH3:39])([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26].C(N[C@H](C(N[C@H](C(O)=O)CC(C)C)=O)CC(C)C)(OCC1C=CC=CC=1)=O>>[CH2:28]([O:27][C:25]([NH:35][C@@H:36]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:7]([NH:9][CH2:10][C:15]1[S:16][CH:17]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:19]=1)=[O:8])=[O:26])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 4

HCID 297MethaneHCID 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-(4carboethoxythiazol-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-225e59585228446e8709ea3d1989875a
Source dataset
uspto-grants-2003_07
Patent number
US06586466B2

Reaction notes

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