L-Isoserine → (S)-2-Hydroxy-3-{[4-hydroxy-7-(3-phenyl-ureido)-isoquinoline-3-carbonyl]-amino}-propionic acid

HRID 1481128Notes

Reaction equation

C(O[C:4]([C:6]1[N:7]=[CH:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([NH:17][C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])[CH:10]=2)=[O:5])C.[NH2:27][CH2:28][C@@H:29]([C:31]([OH:33])=[O:32])[OH:30]>>[OH:30][C@@H:29]([CH2:28][NH:27][C:4]([C:6]1[N:7]=[CH:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([NH:17][C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])[CH:10]=2)=[O:5])[C:31]([OH:33])=[O:32]

Participants

Reactant 2

HCID 6999797L-Isoserine

HCID 898131284-Hydroxy-7-(3-phenyl-ureido)-isoquinoline-3-carboxylic acid ethyl ester

Product 1

HCID 71736258(S)-2-Hydroxy-3-{[4-hydroxy-7-(3-phenyl-ureido)-isoquinoline-3-carbonyl]-amino}-propionic acid

Procedure

(S)-2-Hydroxy-3-{[4-hydroxy-7-(3-phenyl-ureido)-isoquinoline-3-carbonyl]-amino}-propionic acid was prepared from 4-Hydroxy-7-(3-phenyl-ureido)-isoquinoline-3-carboxylic acid ethyl ester from under conditions analogous to Example 116(b) using (S)-isoserine. MS ESI(+) m/e: 411.0449 (M+1).

Sources & evidence

ORD record: ord-e699f8644a9f4459aa5dae2322d64481
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409892B2

Reaction notes

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