Potassium Bromide → (1S,9S)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-carboxylic acid

HRID 2230442Notes

Reaction equation

HRID 2230442 reaction equation
[O:1]=[C:2]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]([O:12][CH2:13][CH:14]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:11])[C:5](=[O:27])[N:4]2[C@H:28]([C:32]([O:34]C(C)(C)C)=[O:33])[CH2:29][CH2:30][CH2:31][N:3]12.C(N[C@@H]1C(=O)N2[C@H](C(O)=O)CCCN2C(=O)CC1)(=O)C1C=CC=CC=1.[K+].[Br-]>C(Cl)Cl>[O:1]=[C:2]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]([O:12][CH2:13][CH:14]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[C:21]3[C:26]2=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:11])[C:5](=[O:27])[N:4]2[C@H:28]([C:32]([OH:34])=[O:33])[CH2:29][CH2:30][CH2:31][N:3]12

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 183965489(S)-benzoylamino-octahydro-6,10-dioxo-6H-pyridazino[1,2-a][1,2]diazepine-1(S)-carboxylic acidHCID 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-carboxylate

Product 1

HCID 18396546(1S,9S)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-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

was prepared from 211f in 96% yield by the same method as for 212e: mp 120-126° C.; [α]D25 −72.5° (c 0.1, CH2Cl2). IR (KBr) 3406, 2950, 1725, 1670, 1526, 1449, 1421, 1272, 1248, 1223, 1175, 761, 741; 1H NMR (CDCl3) δ7.76 (2H, m), 7.62-7.26 (4H, m), 6.07, 5.76 (2H, brs, d, d, J=2.9), 5.46, 5.36 (1H, 2m), 4.79-4.54 (2H, m), 4.77 (2H, m), 4.21 (1H, m), 3.41 (1H, m), 2.89 (1H, m), 2.69 (1H, m), 2.35 (2H, m), 1.98, 1.73 (4H, 2m). MS (ES−, m/z) 462 (M+−1, 50%), 240 (100%).

Sources & evidence

ORD record
ord-0c95c8a76fff4eddadb9a0a83c8cde4c
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

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