Trifluoroacetic acid → HCID 59520224, compound

HRID 1162553Notes

Reaction equation

C([O:5][C:6](=[O:34])[CH2:7][CH2:8][N:9]([CH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1)[C:10]1[S:11][CH:12]=[C:13]([C:15](O)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:14]=1)(C)(C)C.C(O)(C(F)(F)F)=O.[SiH](CC)(CC)CC>>[CH:15]([C:13]1[N:14]=[C:10]([N:9]([CH:29]2[CH2:30][CH2:31][CH2:32][CH2:33]2)[CH2:8][CH2:7][C:6]([OH:34])=[O:5])[S:11][CH:12]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 12052Triethylsilane

HCID 68648247HCID 68648247, compound

Product 1

HCID 59520224HCID 59520224, compoundYield 40.4%

Procedure

The above alcohol (131 mg, 0.274 mmol), TFA (2.0 mL) and Et3SiH (0.23 mL) were combined according to general procedure O. After aqueous workup the residue was purified by silica gel chromatography (gradient, hexane→1/1 EtOAc-hexane). After concentration and trituration from hexane, 3-[(4-Benzhydryl-thiazol-2-yl)-cyclopentyl-amino]-propionic acid (45 mg, 40%) was obtained. LCMS m/z: 408 (M+1). The HCl salt was also prepared, using general procedure G2, by the addition of 4 M HCl in dioxane.

Workup

customAfter aqueous workup the residue was purified by silica gel chromatography (gradient, hexane→1/1 EtOAc-hexane)
concentrationAfter concentration and trituration from hexane

Sources & evidence

ORD record: ord-bb8e909f23984b0ea044c049004336c3
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820704B2

Reaction notes

Loading…