HCID 70982631, compound → HCID 71003692, compound

HRID 2272663Notes

Reaction equation

HRID 2272663 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 70982631HCID 70982631, compound

Product 1

HCID 71003692HCID 71003692, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (4R)-4-[(1R)-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-[(1R)-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 7.69 (d, J=3.2 Hz, 1H), 7.54 (d, J=3.2 Hz, 1H), 7.35 (s, 1H), 6.12 (s, 1H), 3.08 (dd, J=9.1, 7.3 Hz, 1H), 2.96-2.86 (m, 1H), 2.82 (t, J=9.0 Hz, 1H), 2.22 (dd, J=16.8, 8.7 Hz, 1H), 2.14 (dd, J=16.8, 9.6 Hz, 1H), 1.42 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-e6e2cbbdc1ac43f5a17a53b94a4a7ab8
Source dataset
uspto-grants-2015_09
Patent number
US09120785B2

Reaction notes

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