(S)-Benzyl 2-amino-3-(4-hydroxyphenyl)propanoate → N-(4-Carboxy-2-methylbutanoyl)-L-tyrosine

HRID 262278Notes

Reaction equation

HRID 262278 reaction equation
C(OC(=O)[C@H](CC1C=CC(O)=CC=1)N)C1C=CC=CC=1.C(OC(=O)[C@H](C)N)C1C=CC=CC=1.C([O:41][C:42](=[O:63])[C@H:43]([CH2:55][C:56]1[CH:61]=[CH:60][C:59]([OH:62])=[CH:58][CH:57]=1)[NH:44][C:45](=[O:54])[CH:46]([CH3:53])[CH2:47][CH2:48][C:49]([O:51]C)=[O:50])C1C=CC=CC=1.COC(CCC(C)C(N[C@H](C(O)=O)CC1C=CC(O)=CC=1)=O)=O>>[C:49]([CH2:48][CH2:47][CH:46]([CH3:53])[C:45]([NH:44][C@H:43]([C:42]([OH:63])=[O:41])[CH2:55][C:56]1[CH:57]=[CH:58][C:59]([OH:62])=[CH:60][CH:61]=1)=[O:54])([OH:51])=[O:50]

Participants

5

Reactant 4

HCID 104541(S)-Benzyl 2-amino-3-(4-hydroxyphenyl)propanoateHCID 726858benzyl (2S)-2-aminopropanoateHCID 54358394N-(4-methoxycarbonyl-2-methylbutanoyl)-L-tyrosineHCID 54526057N-(4-methoxycarbonyl-2-methylbutanoyl)-L-tyrosine benzyl ester

Product 1

HCID 54098449N-(4-Carboxy-2-methylbutanoyl)-L-tyrosine

Procedure

By substituting L-tyrosine benzyl ester for the L-alanine benzyl ester in the procedure of Example 23, and then treating the product by the procedure of Examples 24 and 26, N-(4-methoxycarbonyl-2-methylbutanoyl)-L-tyrosine benzyl ester, N-(4-methoxycarbonyl-2-methylbutanoyl)-L-tyrosine, and N-(4-carboxy-2-,ethylbutanoyl)-L-tyrosine are obtained.

Workup

  1. customare obtained

Sources & evidence

ORD record
ord-916a169438784c9694befe85ceba0b90
Source dataset
uspto-grants-1979_05
Patent number
US04153725

Reaction notes

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