Phosphoric Acid → HCID 54674530, compound

HRID 1626940Notes

Reaction equation

HRID 1626940 reaction equation
[NH2:1][C@H:2]([CH2:20][C:21]1[CH:26]=[C:25]([F:27])[C:24]([F:28])=[CH:23][C:22]=1[F:29])[CH2:3][C:4]([N:6]1[CH2:10][CH2:9][C@H:8]2[CH2:11][N:12]([C:14](=[O:19])[C:15]([F:18])([CH3:17])[CH3:16])[CH2:13][C@@H:7]12)=[O:5].[P:30](=[O:34])([OH:33])([OH:32])[OH:31]>C(O)C>[P:30]([OH:34])([OH:33])([OH:32])=[O:31].[NH2:1][C@H:2]([CH2:20][C:21]1[CH:26]=[C:25]([F:27])[C:24]([F:28])=[CH:23][C:22]=1[F:29])[CH2:3][C:4]([N:6]1[CH2:10][CH2:9][C@H:8]2[CH2:11][N:12]([C:14](=[O:19])[C:15]([F:18])([CH3:16])[CH3:17])[CH2:13][C@@H:7]12)=[O:5]

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 54674381HCID 54674381, compound

Product 1

HCID 54674530HCID 54674530, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Free base (R)-3-amino-1-((3aS,6aS)-5-(2-fluoro-2-methylpropionyl)-hexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one compound 7 (100 mg, 0.24 mmol) obtained from example 7 was dissolved in ethanol (0.5 mL), added dropwise into phosphoric acid (24 mg, 0.24 mmol) in ethanol solution (1 mL), stirred until precipitation of white solid, filtered to give (R)-3-amino-1-((3aS,6aS)-5-(2-fluoro-2-methylpropionyl)-hexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one phosphate compound 10 (84 mg, 84%) as white powder. MS m/z (ESI): 416.4 (M+1), 438.2 (M+Na). 1H NMR (D2O, 400 MHz): δ 1.62 (m, 6H), 1.96 (m, 1H), 2.20 (m, 1H), 2.78-2.91 (m, 2H), 3.05-3.30 (m, 3H), 3.42-3.83 (m, 6H), 3.96 (m, 2H), 7.20 (m, 1H), 7.35 (m, 1H).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-c45fa52020c04bbdb95dc1f93ab0955e
Source dataset
uspto-grants-2014_07
Patent number
US08785477B2

Reaction notes

Loading…