Trifluoroacetic acid → 4-(2-Amino-3-tert-butoxy-butyryl)-3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

HRID 1949629Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([F:25])=[CH:22][CH:23]=3)[NH:18][CH:17]=2)[CH:13]2[N:26]([C:29](=[O:46])[CH:30]([NH:38]C(OC(C)(C)C)=O)[CH:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH3:32])[CH2:27][CH2:28][CH:12]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([F:25])=[CH:22][CH:23]=3)[NH:18][CH:17]=2)[CH:13]2[N:26]([C:29](=[O:46])[CH:30]([NH2:38])[CH:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])[CH3:32])[CH2:27][CH2:28][CH:12]12)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution containing crude 43 (340 mg, 0.53 mmol) in DCM (10 mL) was cooled to 0° C. TFA (3 mL) was added. After 2 h, the reaction mixture was quenched by the slow addition of cold, aqueous K2CO3. The reaction mixture was extracted with DCM and the resultant organic phase was washed successively with saturated aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 283 mg of 44 as an amber-colored foam which was used without further purification. Mass spectrum, m/z [537.3] (M+H)+.

Workup

customthe reaction mixture was quenched by the slow addition of cold, aqueous K2CO3
extractionThe reaction mixture was extracted with DCM
washthe resultant organic phase was washed successively with saturated aqueous NaHCO3 and brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-0e41e655ca784a19a5e91e4ad0d87468
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399683B2

Reaction notes

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