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

HRID 2230438Notes

Reaction equation

C([NH:9][C@@H:10]1[C:16](=[O:17])[N:15]2[C@H:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:19][CH2:20][CH2:21][N:14]2[C:13](=[O:29])[CH2:12][CH2:11]1)(=O)C1C=CC=CC=1.[CH:30]1[C:42]2[CH:41]([CH2:43][O:44][C:45](Cl)=[O:46])[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34]=2[CH:33]=[CH:32][CH:31]=1>>[O:29]=[C:13]1[CH2:12][CH2:11][C@H:10]([NH:9][C:45]([O:44][CH2:43][CH:41]2[C:40]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:34]3[C:42]2=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:46])[C:16](=[O:17])[N:15]2[C@H:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:19][CH2:20][CH2:21][N:14]12

Participants

Reactant 2

HCID 343679-Fluorenylmethyl chloroformate

HCID 57166602(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

Product 1

HCID 67022165(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-carboxylateYield 89%

Procedure

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%).

Sources & evidence

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

Reaction notes

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