L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- → Dl-Phenylalanine

HRID 1252835Notes

Reaction equation

HRID 1252835 reaction equation
SCCC(N1CCC[C@H]1C(O)=O)=O.C([NH:21][C@@H:22]([C:30]([OH:32])=[O:31])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(OC(C)(C)C)=O.C([NH:40][C@H:41]([C:49]([OH:51])=[O:50])[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)(OC(C)(C)C)=O>>[NH2:21][C@@H:22]([C:30]([OH:32])=[O:31])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[NH2:40][C@H:41]([C:49]([OH:51])=[O:50])[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.[NH2:21][CH:22]([C:30]([OH:32])=[O:31])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 999781-(3-Mercapto-1-oxopropyl)-L-prolineHCID 637610Boc-D-phenylalanine

Product 3

HCID 994Dl-PhenylalanineHCID 6140L-PhenylalanineHCID 71567D-Phenylalanine

Procedure

The desired compounds are prepared by substituting 2-mercaptopropanoyl-L-proline and 3-mercaptopropanoyl-L-proline for 2-D-methyl-3-mercaptopropanoyl-L-proline in the procedures of each of Examples 196-198, and reacting the mercapto compound with either Boc-D-phenylalanine, Boc-L-phenylalanine, or a 50:50 mixture thereof, to form the desired D-Phe, L-Phe or D,L-Phe derivative.

Sources & evidence

ORD record
ord-5ee857c7f89641e58270234d5895151e
Source dataset
uspto-grants-1988_05
Patent number
US04745124

Reaction notes

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