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

HRID 2270461Notes

Reaction equation

HRID 2270461 reaction equation
[NH2:1][CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=1.NC(C1SC=C(C(OCC)=O)N=1)CC(C)C.[C:29]([NH:39][C@H:40]([C:45](O)=[O:46])[CH2:41][CH:42]([CH3:44])[CH3:43])([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30].C(N[C@H](C(N[C@H](C(O)=O)CC(C)C)=O)CC(C)C)(OCC1C=CC=CC=1)=O>>[CH2:32]([O:31][C:29]([NH:39][C@@H:40]([CH2:41][CH:42]([CH3:44])[CH3:43])[C:45]([NH:1][CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=1)=[O:46])=[O:30])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 4

HCID 74840Leucine, N-carboxy-, N-benzyl ester, L-HCID 7299379N-((Phenylmethoxy)carbonyl)-L-leucyl-L-leucineHCID 10442432Ethyl 2-(aminomethyl)-1,3-thiazole-4-carboxylateHCID 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 of Example 13, except substituting 1-tert-butoxycarbonyl)amino-1-(4-carboethoxythiazol-2yl)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-5a446a71ab514e00ae81ab08667cb52a
Source dataset
uspto-grants-2001_12
Patent number
US06331542B1

Reaction notes

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