Tetrabutylammonium Fluoride → (S)-2-(2,6-dichloro-4-hydroxy-benzoylamino)-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester

HRID 63740

Reaction equation

[CH2:1]([O:4][C:5](=[O:47])[C@@H:6]([NH:25][C:26](=[O:46])[C:27]1[C:32]([Cl:33])=[CH:31][C:30]([O:34][Si](C(C)C)(C(C)C)C(C)C)=[CH:29][C:28]=1[Cl:45])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15](=[O:24])[N:16]([CH3:23])[C:17](=[O:22])[N:18]([CH3:21])[C:19]=2[CH3:20])=[CH:10][CH:9]=1)[CH2:2][CH3:3].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[CH2:1]([O:4][C:5](=[O:47])[C@@H:6]([NH:25][C:26](=[O:46])[C:27]1[C:28]([Cl:45])=[CH:29][C:30]([OH:34])=[CH:31][C:32]=1[Cl:33])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[C:15](=[O:24])[N:16]([CH3:23])[C:17](=[O:22])[N:18]([CH3:21])[C:19]=2[CH3:20])=[CH:12][CH:13]=1)[CH2:2][CH3:3]

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 89721092(S)-2-(2,6-dichloro-4-triisopropylsilanyloxy-benzoylamino)-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester

Product 1

HCID 89720687(S)-2-(2,6-dichloro-4-hydroxy-benzoylamino)-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester

Procedure

The title compound was prepared using a similar procedure as described in Example 5, Step 4, starting from (S)-2-(2,6-dichloro-4-triisopropylsilanyloxy-benzoylamino)-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester (1.66 g, 2.35 mmol) and TBAF (3.5 mL, 3.5 mmol, 1M), and after ISCO column chromatography purification, resulted in a white solid (884 mg, 69%). ES(+)-LRMS m/e calcd. for C26H27Cl2N3O6 (M+H)+ 548, obsd. 548.

Workup

customafter ISCO column chromatography purification

Sources & evidence

ORD record: ord-4952f93a9b2249bb81999aa33d8dd3fe
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447035B2

Linked notes

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