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

HRID 1107062Notes

Reaction equation

HRID 1107062 reaction equation
C.[NH2:2][CH:3]([C:8]1[S:9][CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:12]=1)CC(C)C.[C:18]([NH:28][C@H:29]([C:34](O)=[O:35])[CH2:30][CH:31]([CH3:33])[CH3:32])([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].C(N[C@H](C(N[C@H](C(O)=O)CC(C)C)=O)CC(C)C)(OCC1C=CC=CC=1)=O>>[CH2:21]([O:20][C:18]([NH:28][C@@H:29]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:34]([NH:2][CH2:3][C:8]1[S:9][CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:12]=1)=[O:35])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 4

HCID 297MethaneHCID 74840Leucine, N-carboxy-, N-benzyl ester, L-HCID 7299379N-((Phenylmethoxy)carbonyl)-L-leucyl-L-leucineHCID 76155321Amino-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-331ead0ca30c405087171d3420fed1c4
Source dataset
uspto-grants-2000_05
Patent number
US06057362

Reaction notes

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