D-Lactic Acid → (2R)-1-[5-{1-[(2,2-Difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridin-5-yl}hexahydrocyclopenta[c]pyrrol-2(1H)-yl]-1-oxopropan-2-ol

Participants

Role	Name	HCID	Charge
Reactant	D-Lactic Acid	HCID 61503	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	1-[(2,2-Difluorocyclopropyl)methyl]-3-methyl-5-(octahydrocyclopenta[c]-pyrrol-5-yl)-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridine 2,2-dioxide	HCID 71140748	—
Solvent	Acetonitrile	HCID 6342	—
Product	(2R)-1-[5-{1-[(2,2-Difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridin-5-yl}hexahydrocyclopenta[c]pyrrol-2(1H)-yl]-1-oxopropan-2-ol	HCID 71140749	—

Reaction Steps

1-[(2,2-Difluorocyclopropyl)methyl]-3-methyl-5-(octahydrocyclopenta[c]-pyrrol-5-yl)-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridine 2,2-dioxide (25-1, 20 mg, 0.052 mmol, 1.0 equiv), (2R)-2-hydroxypropanoic acid (25-2, 7.0 mg, 0.078 mmol, 1.5 equiv), DIPEA (27 μL, 0.16 mmol, 3.0 equiv) and HATU (29.7 mg, 0.078 mmol, 1.5 equiv) were added to anhydrous acetonitrile (520 μL). After stirring for 10 min at room temperature, LCMS showed consumption of starting material. Purification by reverse-phase HPLC (20-100% CH3CN:0.1% TFA in H2O) provided 25-3 as a white solid. MS m/z (M+H): calculated=457.1716; observed=457.1726.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09315518B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-53f82aa06da34563b3b329cbd064ade0
Source note	uspto-grants-2016_04