Water → HCID 59272309, compound

HRID 1970257Notes

Reaction equation

[CH3:1][C:2]([CH3:31])([CH3:30])[C:3]#[C:4][C:5]1[CH:18]=[CH:17][C:16]2[O:15][C:14]3[C:9](=[CH:10][C:11]([C:19]4[CH:20]=[N:21][CH:22]=[N:23][CH:24]=4)=[CH:12][CH:13]=3)[C@@:8]3([CH2:28][O:27][C:26]([NH2:29])=[N:25]3)[C:7]=2[CH:6]=1.[OH2:32]>C(O)(C(F)(F)F)=O>[NH2:29][C:26]1[O:27][CH2:28][C@@:8]2([N:25]=1)[C:7]1[CH:6]=[C:5]([C:4](=[O:32])[CH2:3][C:2]([CH3:31])([CH3:30])[CH3:1])[CH:18]=[CH:17][C:16]=1[O:15][C:14]1[C:9]2=[CH:10][C:11]([C:19]2[CH:20]=[N:21][CH:22]=[N:23][CH:24]=2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 40 °C

Procedure

(4R)-2′-(3,3-Dimethylbut-1-ynyl)-7′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (70 mg, 171 μmol) was dissolved in TFA (1.31 ml) at RT and water (31 μl, 1705 μmol) was added. The mixture then was heated at 40° C. for 1 hr. TFA was removed in a stream of nitrogen and yellow residue was treated with 1.5 ml of 2N ammonia in methanol for 15 min at RT. The solution was concentrated in vacuo, residue was diluted with ethyl acetate (5 ml), the solution was washed with saturated NaHCO3 solution, brine, dried with magnesium sulfate and concentrated to give 1-((4S)-2-amino-7′-(5-pyrimidinyl)spiro[1,3-oxazole-4,9′-xanthen]-2′-yl)-3,3-dimethyl-1-butanone.

Workup

customTFA was removed in a stream of nitrogen and yellow residue
additionwas treated with 1.5 ml of 2N ammonia in methanol for 15 min at RT
concentrationThe solution was concentrated in vacuo, residue
additionwas diluted with ethyl acetate (5 ml)
washthe solution was washed with saturated NaHCO3 solution, brine
dry with materialdried with magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-4cad63024491464c8d6d5cb5b2bbcfdb
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426447B2

Reaction notes

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