HCID 9874017, compound → HCID 9894984, compound

HRID 987212Notes

Reaction equation

HRID 987212 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8]CCCCC[O:14]C1C=CC2N(C(=O)C(C(NC[C@H](NS(C3C=CC=CC=3)(=O)=O)C(O)=O)=O)=CC=2)C=1.C([O:48][C:49](=[O:88])[C@@H:50]([NH:78][S:79]([C:82]1[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=1)(=[O:81])=[O:80])[CH2:51][NH:52][C:53]([C:55]1[C:64](=[O:65])[N:63]2[C:58]([CH:59]=[CH:60][C:61]([O:66][CH2:67][CH2:68][CH2:69][NH:70]C(OC(C)(C)C)=O)=[CH:62]2)=[CH:57][CH:56]=1)=[O:54])(C)(C)C>C(O)C>[CH2:3]([OH:4])[CH3:2].[OH-:14].[NH4+:8].[OH2:48].[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:70][CH2:69][CH2:68][CH2:67][O:66][C:61]1[CH:60]=[CH:59][C:58]2[N:63]([C:64](=[O:65])[C:55]([C:53]([NH:52][CH2:51][C@H:50]([NH:78][S:79]([C:82]3[CH:83]=[CH:84][CH:85]=[CH:86][CH:87]=3)(=[O:81])=[O:80])[C:49]([OH:88])=[O:48])=[O:54])=[CH:56][CH:57]=2)[CH:62]=1

Participants

6

Reactant 2

HCID 9874017HCID 9874017, compoundHCID 56624168HCID 56624168, compound

Product 3

HCID 6422Trifluoroacetic acidHCID 9894984HCID 9894984, compoundYield 36%HCID 86596525Ethanol ammonium hydroxide water

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the procedure described in step E for the preparation of compound I, 38 mg (0.059 mmol) of (S)-2-benzenesulfonylamino-3-{[7-(3-tert-butoxycarbonylaminopropoxy)-4-oxo-4H-quinolizine-3-carbonyl]-amino}-propionic acid tert-butyl ester afforded after flash chromatography (ethanol to ethanol:ammonium hydroxide:water (8:1:1) and treatment with trifluoroacetic acid, 12 mg (36% yield) of pure desired product which was characterized with 1HNMR (400 MHz, D2O) δ: 2.25-2.29 (m, 2H), 3.26-3.31 (t, J=6.5 Hz, 1H), 3.42-3.50 (dd, J=10.0 and 13.5 Hz, 1H), 3.84-3.90 (dd, J=14.5 and 4.0 Hz, 1H), 4.23-4.26 (m, 3H), 6.90-6.94 (m, 2H), 7.04-7.10 (m, 2H), 7.56 (d, J=9.5 Hz, 1H), 7.64 (d, J=7.5 Hz, 2H), 7.69-7.75 (m, 1H), 7.91 (d, J=8.5 Hz, 1H).

Sources & evidence

ORD record
ord-7d3c42f15b994bccb41689bc38c240f8
Source dataset
uspto-grants-2003_10
Patent number
US06630488B1

Reaction notes

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