N-Acetylisoleucine → N-Acetyl-L-Ile-L-Tyr-(R)-1-Amino-2-(4-Hydroxyphenyl)ethylphosphonic Acid

HRID 653467Notes

Reaction equation

[C:1]([NH:4][C@H:5]([C:10]([OH:12])=O)[C@H:6]([CH2:8][CH3:9])[CH3:7])(=[O:3])[CH3:2].C([O:20][C:21]1[CH:52]=[CH:51][C:24]([CH2:25][C@@H:26]([C:28]([NH:30][C@H:31]([P:47](=[O:50])([OH:49])[OH:48])[CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39]CC3C=CC=CC=3)=[CH:35][CH:34]=2)=[O:29])[NH2:27])=[CH:23][CH:22]=1)C1C=CC=CC=1>>[C:1]([NH:4][C@H:5]([C:10]([NH:27][C@H:26]([C:28]([NH:30][C@H:31]([P:47](=[O:48])([OH:50])[OH:49])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)=[O:29])[CH2:25][C:24]1[CH:23]=[CH:22][C:21]([OH:20])=[CH:52][CH:51]=1)=[O:12])[C@H:6]([CH2:8][CH3:9])[CH3:7])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 7036275N-Acetylisoleucine

HCID 18608402N-(O-benzyl-L-tyrosyl)-(R)-(-)-1-amino-2-(4-benzyloxyphenyl)ethylphosphonic acid

Product 1

HCID 18608377N-Acetyl-L-Ile-L-Tyr-(R)-1-Amino-2-(4-Hydroxyphenyl)ethylphosphonic Acid

Procedure

Diethyl ester of N-(N-acetyl-L-isoleucyl-L-tyrosyl)-(R)-(-)-1-amino-2-(4-hydroxyphenyl)ethylphosphonic acid was synthesized from N-acetyl-L-isoleucine and the compound 46a in the same condensation procedure as in Example 1 and then through the same reaction and treatment as in Example 8.

Workup

customthrough the same reaction and treatment as in Example 8

Sources & evidence

ORD record: ord-823b5f17fe5549c89d8c8c5c30bad4c3
Source dataset: uspto-grants-1987_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04677125

Reaction notes

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