Benzylamine → (1r,2s)-1-{[(2s,4r)-1-((1S)-1-benzylcarbamoyl-2-methyl-propylcarbamoyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid

HRID 1822447Notes

Reaction equation

HRID 1822447 reaction equation
C(OC(N[C@H](C(O)=O)C(C)C)=O)(C)(C)C.C(OC(NC(C(C)(C)C)C(O)=O)=O)(C)(C)C.C(N)C1C=CC=CC=1.C(OC(=O)NC(C(=O)NC1C2C(=CC=CC=2)CC1O)C(C)(C)C)(C)(C)C.ClNC(=O)[O-].C([O:73][C:74]([C:76]1([NH:81][C:82]([CH:84]2[CH2:88][CH:87]([O:89][C:90]3[C:99]4[C:94](=[CH:95][C:96]([O:100][CH3:101])=[CH:97][CH:98]=4)[N:93]=[C:92]([C:102]4[CH:107]=[CH:106][CH:105]=[CH:104][CH:103]=4)[CH:91]=3)[CH2:86][N:85]2[C:108](=[O:128])[NH:109][CH:110]([C:115](=[O:127])[NH:116][CH:117]2[C:125]3[C:120](=[CH:121][CH:122]=[CH:123][CH:124]=3)CC2O)[C:111](C)([CH3:113])[CH3:112])=[O:83])[CH2:78][CH:77]1[CH:79]=[CH2:80])=[O:75])C>>[CH2:117]([NH:116][C:115]([C@@H:110]([NH:109][C:108]([N:85]1[CH2:86][C@H:87]([O:89][C:90]2[C:99]3[C:94](=[CH:95][C:96]([O:100][CH3:101])=[CH:97][CH:98]=3)[N:93]=[C:92]([C:102]3[CH:103]=[CH:104][CH:105]=[CH:106][CH:107]=3)[CH:91]=2)[CH2:88][C@H:84]1[C:82]([NH:81][C@:76]1([C:74]([OH:75])=[O:73])[CH2:78][C@H:77]1[CH:79]=[CH2:80])=[O:83])=[O:128])[CH:111]([CH3:113])[CH3:112])=[O:127])[C:125]1[CH:120]=[CH:121][CH:122]=[CH:123][CH:124]=1

Participants

7

Reactant 6

HCID 7504BenzylamineHCID 83693Boc-L-ValineHCID 50468592-{[(Tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 22035886ChlorocarbamateHCID 68488177[1-(2-Hydroxy-indan-1-ylcarbamoyl)-2,2-dimethyl-propyl]-carbamic acid tert.butyl esterHCID 684916281-{[1-[1-(2-Hydroxy-indan-1-ylcarbamoyl)-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 68490854(1r,2s)-1-{[(2s,4r)-1-((1S)-1-benzylcarbamoyl-2-methyl-propylcarbamoyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid

Procedure

N-(tert-butoxycarbonyl)-L-valine was attached to the resin as described for the preparation of compound 16 followed by reaction with benzylamine as described for the preparation of 17 and removal of the Boc group as described for 18. The afforded compound was then reacted with the chlorocarbamate achieved from 12 as described for the preparation of 13 which gave the title compound. Purity by HPLC>95%. M+H+706.2.

Sources & evidence

ORD record
ord-fc50f8ba6a3240d48b71c93c077b4da9
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

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