Trifluoroacetic acid → 3(R)-[3-[(4-cyanophenyl)acetyl]-1H-pyrrol-1-yl]-N-[2,2-dimethyl-1(S)-(methylcarbamoyl)propyl]succinamic acid allyl ester

HRID 382152Notes

Reaction equation

HRID 382152 reaction equation
C(OC(=O)CC(N1C=CC(C2C=CC=CC=2)=C1)C(N[CH:15]1[CH2:31][C:30]2=CN([C:24]3[C:29]2=[CH:28][CH:27]=[CH:26][CH:25]=3)CCO[CH2:19][CH2:18][NH:17][C:16]1=O)=O)C1C=CC=CC=1.FC(F)(F)C(O)=O.[CH2:53]([O:56][C:57](=[O:73])[C@H:58](N)[CH2:59][C:60]([NH:62][C@H:63]([C:68](=[O:71])[NH:69][CH3:70])[C:64]([CH3:67])([CH3:66])[CH3:65])=[O:61])[CH:54]=[CH2:55].[C:74](C1C=CC(C#CC2CC(OC)OC2OC)=CC=1)#[N:75].FC(F)(F)C(O)=[O:96]>CCCCCCC.CC(O)=O>[CH2:53]([O:56][C:57](=[O:73])[CH2:58][C@@H:59]([N:17]1[CH:18]=[CH:19][C:15]([C:31](=[O:96])[CH2:30][C:29]2[CH:28]=[CH:27][C:26]([C:74]#[N:75])=[CH:25][CH:24]=2)=[CH:16]1)[C:60]([NH:62][C@H:63]([C:68](=[O:71])[NH:69][CH3:70])[C:64]([CH3:67])([CH3:66])[CH3:65])=[O:61])[CH:54]=[CH2:55]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 18341503N-(8-oxo-4-oxa-1,7-diaza-tricyclo-[9.6.1.012,17]-octadeca-11(18), 12,14,16-tetraen-9-yl)-3-(3-phenyl-1H-pyrrol-1-yl)succinamic acid benzyl esterHCID 183803483-[2-(4-Cyanophenyl)-ethynyl]-2,5-dimethoxy-tetrahydrofuranHCID 86757527(R)-amino-N-(2,2-dimethyl-1(S)-(methylcarbamoyl)propyl)succinamic acid allyl ester trifluoroacetate salt

Product 1

HCID 700987653(R)-[3-[(4-cyanophenyl)acetyl]-1H-pyrrol-1-yl]-N-[2,2-dimethyl-1(S)-(methylcarbamoyl)propyl]succinamic acid allyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8900HeptaneSolvent

Procedure

As described in Example 1(c) for the preparation of N-(8-oxo-4-oxa-1,7-diaza-tricyclo[9.6. 1.012,17]octadeca-11 (18),12,14,16-tetraen-9-yl)-3-(3-phenyl-1H-pyrrol-1-yl)succinamic acid benzyl ester, 3 (R)-amino-N-(2,2-dimethyl-1(S)-(methylcarbamoyl)propyl)succinamic acid allyl ester trifluoroacetate salt and 3-[2-(4-cyanophenyl)-ethynyl]-2,5-dimethoxy-tetrahydrofuran were heated with trifluoroacetic acid (1 equiv) at 70° C. for 4 hours. Flash column chromatography twice with 0.5% HOAc/15% EtOAc/CH2Cl2 as eluant and azeotrope with n-heptane afforded 800 mg (36%, 43% based on recovered furan) of 3(R)-[3-[(4-cyanophenyl)acetyl]-1H-pyrrol-1-yl]-N-[2,2-dimethyl-1(S)-(methylcarbamoyl)propyl]succinamic acid allyl ester as a brown oil.

Sources & evidence

ORD record
ord-98461840fa4e4b8a938d84df77079869
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

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