Potassium Bromide → (1S,9S)-9-(benzyloxycarbonylamino)-6,10-dioxo octahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid

HRID 2230440Notes

Reaction equation

HRID 2230440 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C:18](=[O:19])[N:17]2[C@H:20]([C:24]([O:26]C(C)(C)C)=[O:25])[CH2:21][CH2:22][CH2:23][N:16]2[C:15](=[O:31])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K+].[Br-]>CO>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C:18](=[O:19])[N:17]2[C@H:20]([C:24]([OH:26])=[O:25])[CH2:21][CH2:22][CH2:23][N:16]2[C:15](=[O:31])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 253877Potassium BromideHCID 67022104(1S,9S)-tert-butyl 9-(benzyloxycarbonylamino)-6,10-dioxooctahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate

Product 1

HCID 18396550(1S,9S)-9-(benzyloxycarbonylamino)-6,10-dioxo octahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

was prepared from 211d by the same method as compound 212e as colourless crystals (170 mg, 97%): mp 60-100° C.; [α]D22 −103 (c 0.10, MeOH); IR (KBr) 3341, 2947, 1728, 1675, 1531, 1456, 1422, 1339, 1272, 1248, 1221, 1174, 1122, 1056, 982, 639; 1H NMR CDCl3) δ7.35 (5H, s), 5.65 (1H, d), 5.48-5.40 (1H, m), 5.10 (2H, s), 4.76-4.57 (2H, m), 3.49-3.30 (2H, m), 2.92-2.59 (2H, m), 2.40-2.27 (2H, m), 1.97-1.67 (4H, m); MS (ES−) 374 (M−1, 100%). Accurate mass calculated for C18H22N3O6 (MH+): 376.1509. Found: 376.1483. Accurate mass calculated for C18H21N3O6Na (MNa+): 398.1328. Found: 398.1315.

Sources & evidence

ORD record
ord-9d46829e2a2a44c783167801e2f4e5be
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

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