9-Fluorenylmethyl chloroformate → (1S,9S)t-Butyl 6,10-dioxo-9-(fluoren-9-ylmethyloxycarbonylamino)-1,2,3,4,7,8,9,10-octahydro-6H-pyridazino[1,2-a][1,2]-diazepine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	9-Fluorenylmethyl chloroformate	HCID 34367	—
Reactant	(1S, 9S) t-Butyl 9-benzoylamino-6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate	HCID 57166602	—
Product	(1S,9S)t-Butyl 6,10-dioxo-9-(fluoren-9-ylmethyloxycarbonylamino)-1,2,3,4,7,8,9,10-octahydro-6H-pyridazino[1,2-a][1,2]-diazepine-1-carboxylate	HCID 67022165	89%

Reaction Steps

was prepared in a similar manner to 211e, except 9-fluorenylmethylchloroformate was used instead of benzoylchloride to give a white glassy solid 211f (2.14 g, 89%): mp 190-192° C.; [α]D25 −81.5° (c 0.1, CH2Cl2). IR (KBr) 3335, 2977, 1731, 1678, 1450, 1421, 1246, 1156, 742; 1H NMR (CDCl3) δ7.60 (2H, m), 7.57 (2H, m), 7.50-7.26 (4H, m), 5.60 (1H, d, J=7.8), 5.28 (1H, m), 4.67 (2H, m), 4.38 (2H, m), 4.23 (1H, m), 3.59-3.41 (1H, m), 2.92-2.65 (2H, m), 2.41-2.21 (2H, m), 1.95-1.58 (4H, m), 1.47 (9H, s). MS(ES−, m/z) 520 (M++1, 97%), 179 (100%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06423840B1
Source dataset	uspto-grants-2002_07
ORD ID	ord-fcbf32ad40964ccd9e800fd1d1008ab3
Source note	uspto-grants-2002_07