HCID 86715341, compound → HCID 71003691, compound

HRID 2272662Notes

Reaction equation

HRID 2272662 reaction equation
[OH:1][C@@:2]([C@H:9]1[CH2:13][N:12]([C@H](C2C=CC(OC)=CC=2)C)[C:11](=[O:24])[CH2:10]1)([C:4]1[S:5][CH:6]=[CH:7][N:8]=1)[CH3:3]>C(O)(C(F)(F)F)=O.CC(O)C>[OH:1][C@@:2]([C@H:9]1[CH2:13][NH:12][C:11](=[O:24])[CH2:10]1)([C:4]1[S:5][CH:6]=[CH:7][N:8]=1)[CH3:3]

Participants

4

Reactant 1

HCID 86715341HCID 86715341, compound

Product 1

HCID 71003691HCID 71003691, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (4R)-4-[(1S)-1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]-1-[(1S)-1-(4-methoxyphenyl)ethyl]pyrrolidin-2-one (3.6 g, 10.4 mmol) in TFA (10 mL) was heated to 70° C. for 5 hours. The reaction mixture was cooled to room temperature, diluted with IPA (30 mL), and stirred until the color dissipated. The reaction mixture was then absorbed on silica gel and purified by silica gel chromatography to afford (4R)-4-[(1S)-1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]pyrrolidin-2-one. MS ESI calc'd. for C9H13N2O2S [M+H]+ 213. found 213. 1H NMR (600 MHz, DMSO-d6) δ 7.68 (d, J=3.2 Hz, 1H), 7.54 (d, J=3.2 Hz, 1H), 7.39 (s, 1H), 6.10 (s, 1H), 3.25 (t, J=9.2 Hz, 1H), 3.19 (dd, J=9.6, 7.4 Hz, 1H), 2.91-2.81 (m, 1H), 2.20 (dd, J=16.7, 8.6 Hz, 1H), 1.77 (dd, J=16.7, 9.6 Hz, 1H), 1.43 (s, 3H).

Workup

  1. customThe reaction mixture was then absorbed on silica gel
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-2bb50bb2eee74ad9bad9d9faf84220ad
Source dataset
uspto-grants-2015_09
Patent number
US09120785B2

Reaction notes

Loading…