N-Benzyloxycarbonyl-L-prolyl-L-alanine → 1-[(Benzyloxy)carbonyl]-L-prolyl-L-alanyl-N-ethyl-L-alaninamide

HRID 370637Notes

Reaction equation

[N:1]1([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:13][CH2:12][CH2:11][C@H:2]1[C:3]([NH:5][C@H:6]([C:8]([OH:10])=O)[CH3:7])=[O:4].[NH2:24][C@H:25]([C:27]([NH:29][CH2:30][CH3:31])=[O:28])[CH3:26]>>[N:1]1([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:13][CH2:12][CH2:11][C@H:2]1[C:3]([NH:5][C@H:6]([C:8]([NH:24][C@H:25]([C:27]([NH:29][CH2:30][CH3:31])=[O:28])[CH3:26])=[O:10])[CH3:7])=[O:4]

Participants

Reactant 2

HCID 73513N-Benzyloxycarbonyl-L-prolyl-L-alanine

HCID 7128993Alanine ethylamide

Product 1

HCID 137500281-[(Benzyloxy)carbonyl]-L-prolyl-L-alanyl-N-ethyl-L-alaninamide

Procedure

The condensation of Z-Pro-Ala with Ala-NH-Et by the procedure in Example 7 yields Z-Pro-Ala-Ala-NH-Et; m.p. 219°-220° C. from 2-propanol--AcOEt); (α)D20 =-36.2°; c=0.2 (dimethylformamide). This intermediate is successively converted, as described in Example 2, into (1) BOC-Asp(Obzl)-Pro-Ala-Ala-NH-Et, m.p. 133°-136° C. (AcOEt--petroleum ether), (α)D20 =-61.1°, c=0.2 (MeOH); (2) Asp(OBzl)-Pro-Ala-Ala-NH-Et.HCl, m.p. 189°-193° C. (MeOH--Et2O), and (3) Ac-Asp(OBzl(-Pro-Ala-Ala-NH-Et, m.p. 191°-193° C. (AcOEt--petroleum ether), (α)D20 =-68.5°, c=0.2 (MeOH). Hydrogenolysis of the latter product by the procedure in Example 1 yields the title compound, Nα -Acetylaspartyl-prolyl-alanyl-alanine ethylamide; m.p. 153°-155° C. (melting begins at 143° C.).

Sources & evidence

ORD record: ord-afea1b7c62f74572bc15be6b6153749d
Source dataset: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04528133

Reaction notes

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