Isopropanol → HCID 54438717, compound

HRID 370638Notes

Reaction equation

HRID 370638 reaction equation
CC(O)C.CCOC(C)=O.N[C@H](C([N:26]1[CH2:45][CH2:44][CH2:43][C@H:27]1[C:28]([NH:30][C@H:31]([C:33]([NH:35][C@H:36]([C:38]([NH:40][CH2:41][CH3:42])=[O:39])[CH3:37])=[O:34])[CH3:32])=[O:29])=O)CC(=O)OCC1C=CC=CC=1.Cl.[NH:47]([C:56]([CH3:58])=[O:57])[C@H:48]([C:53]([OH:55])=O)[CH2:49][C:50](=[O:52])[OH:51]>CO.CCOCC.CN(C)C=O>[CH2:41]([NH:40][C:38](=[O:39])[C@H:36]([CH3:37])[NH:35][C:33](=[O:34])[C@H:31]([CH3:32])[NH:30][C:28](=[O:29])[C@@H:27]1[CH2:43][CH2:44][CH2:45][N:26]1[C:53](=[O:55])[C@H:48]([CH2:49][C:50](=[O:52])[OH:51])[NH:47][C:56](=[O:57])[CH3:58])[CH3:42]

Participants

8

Reactant 4

HCID 3776IsopropanolHCID 8857Ethyl AcetateHCID 65065(2S)-2-Acetamidobutanedioic acidHCID 131714259HCID 131714259, compound

Product 1

HCID 54438717HCID 54438717, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent3×HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

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.).

Workup

  1. custom(α)D20 =-36.2°

Sources & evidence

ORD record
ord-d7b355e4787843d188627bc372f0f27b
Source dataset
uspto-grants-1985_07
Patent number
US04528133

Reaction notes

Loading…