L-Phenylalanine → N-[2-(Mercaptomethyl)-3-mercaptopropanoyl]-L-phenylalanine

HRID 903512Notes

Reaction equation

[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.N1CCC[C@H]1C(O)=O.[SH:21][CH2:22][CH:23]([CH2:38][SH:39])[C:24](C1(C=CC=CC1)C[C@@H](C(O)=O)N)=[O:25]>>[SH:21][CH2:22][CH:23]([CH2:38][SH:39])[C:24]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:25]

Participants

Reactant 3

HCID 6140L-Phenylalanine2×

HCID 145742L-Proline

HCID 867360361-[2-(mercaptomethyl)-3-mercaptopropanoyl]-L-phenylalanine

Product 1

HCID 54508597N-[2-(Mercaptomethyl)-3-mercaptopropanoyl]-L-phenylalanine

Procedure

By substituting L-phenylalanine for the L-proline in the procedure of Example 3B, and then submitting the product to the procedure of Example 4, 1-[2-acetylthiomethyl)-3-acetylthiopropanoyl]-L-phenylalanine and 1-[2-(mercaptomethyl)-3-mercaptopropanoyl]-L-phenylalanine are obtained.

Workup

customare obtained

Sources & evidence

ORD record: ord-179b4f70d3e9449487e7571974fca3e4
Source dataset: uspto-grants-1980_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04228077

Reaction notes

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