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

HRID 2230441Notes

Reaction equation

HRID 2230441 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([NH:16][C@@H:17]1[C:23](=[O:24])[N:22]2[C@H:25]([C:29]([O:31]C(C)(C)C)=[O:30])[CH2:26][CH2:27][CH2:28][N:21]2[C:20](=[O:36])[CH2:19][CH2:18]1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[C:8]([NH:16][C@@H:17]1[C:23](=[O:24])[N:22]2[C@H:25]([C:29]([OH:31])=[O:30])[CH2:26][CH2:27][CH2:28][N:21]2[C:20](=[O:36])[CH2:19][CH2:18]1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 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 183965489(S)-benzoylamino-octahydro-6,10-dioxo-6H-pyridazino[1,2-a][1,2]diazepine-1(S)-carboxylic acidYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (20 ml) was added to an ice cold stirred solution of the t-butyl ester 211e (4.15 g, 10.34 mmol) in dry CH2Cl2 (20 ml). The mixture was kept cold for 1.5 h then left for 2.5 h at rt, concentrated. TFA was removed by repeated concentrations of CH2Cl2\ether and ether solutions of the residue. Finally trituration of the residue with ether afforded 212e 3.05 g (85%) of a white glassy solid: mp 118-126° C.; [α]D24 −70.5° (c 0.1, CH2Cl2). IR (KBr) 3361, 2943, 1737, 1659, 1537, 1426, 1220, 1174; 1H NMR (CDCl3) δ7.80 (2H, m), 7.54-7.33 (4H, m), 8.83 (brs), 5.44 (1H, m), 5.26-5.13 (1H, m), 4.66 (1H, m), 3.59-3.41 (1H, m), 2.97, 2.76 (2H, 2m), 2.36 (2H, m), 1.98 (2H, m), 1.75 (2H, m). MS(ES−, m/z) 344 (M−1, 100%).

Workup

  1. waitthen left for 2.5 h at rt
  2. concentrationconcentrated
  3. customTFA was removed

Sources & evidence

ORD record
ord-13d09bb675f14bfb8811780ee2c391a6
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

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