N-carbobenzyloxyalanine → Benzyloxycarbonylalanyl-alanyl Proline Propylamide

HRID 1583727Notes

Reaction equation

HRID 1583727 reaction equation
C(NC(=O)[C@H](C)NC(OCC1C=CC=CC=1)=O)C.[CH2:19]([O:26][C:27]([NH:29][C@H:30]([C:32]([OH:34])=O)[CH3:31])=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH2:35]([NH:38][C:39](=[O:50])[C@@H:40]1[CH2:44][CH2:43][CH2:42][N:41]1[C:45](=[O:49])[C@H:46]([CH3:48])[NH2:47])[CH2:36][CH3:37]>CN(C)C=O>[CH2:35]([NH:38][C:39](=[O:50])[C@@H:40]1[CH2:44][CH2:43][CH2:42][N:41]1[C:45](=[O:49])[C@H:46]([CH3:48])[NH:47][C:32](=[O:34])[C@H:30]([CH3:31])[NH:29][C:27]([O:26][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:28])[CH2:36][CH3:37]

Participants

5

Reactant 3

HCID 736104N-carbobenzyloxyalanineHCID 13749958(S)-2-(Cbz-amino)-N-ethylpropanamideHCID 13945022HCID 13945022, compound

Product 1

HCID 13750020Benzyloxycarbonylalanyl-alanyl Proline PropylamideYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared by a process analogous to that employed in preparing benzyloxycarbonyl alanine ethylamide from benzyloxycarbonyl alanine and alanyl proline propylamide in a 71% yield with a melting point of 101 to 103 degrees C. [α]D20 -47.7 degrees (c 0.3; dimethylformamide).

Workup

  1. customThis compound was prepared by a process analogous to

Sources & evidence

ORD record
ord-aa0c8f3f7fce4782be24a2234790b77d
Source dataset
uspto-grants-1985_11
Patent number
US04554100

Reaction notes

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