Trimethylphosphine → HCID 89721028, compound

HRID 63737Notes

Reaction equation

[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]1([C:13]([NH:15][C@@H:16]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[C:28](=[O:37])[N:29]([CH3:36])[C:30](=[O:35])[N:31]([CH3:34])[C:32]=3[CH3:33])=[CH:23][CH:22]=2)[C:17]([OH:19])=[O:18])=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[N+]=[N-].CP(C)C>>[NH2:1][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1([C:13]([NH:15][C@@H:16]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[C:28](=[O:37])[N:29]([CH3:36])[C:30](=[O:35])[N:31]([CH3:34])[C:32]=3[CH3:33])=[CH:25][CH:26]=2)[C:17]([OH:19])=[O:18])=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

Reactant 2

HCID 68983Trimethylphosphine

HCID 89720726(S)-2-[[1-(4-azidobutyl)cyclopentanecarbonyl]amino]-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid

Product 1

HCID 89721028HCID 89721028, compound

Procedure

The title compound was prepared using a similar procedure as described in Example 1, Step 10, starting from (S)-2-[[1-(4-azidobutyl)cyclopentanecarbonyl]amino]-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid (1.02 g, 2 mmol) and trimethylphosphine (8 mL, 8 mmol, 1M) to obtain a white solid (0.96 g, 99%). ES(+)-HRMS m/e calcd. for C26H36N4O5 (M+H)+ 485.2759, obsd. 485.2757.

Sources & evidence

ORD record: ord-674c97f129d74f94a369559f67bc8d46
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447035B2

Reaction notes

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