Cyclohexylamine → HCID 131727702, compound

HRID 1822440Notes

Reaction equation

HRID 1822440 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.C1(N)CCCCC1.C(OC(=O)NC(C(=O)NC1C2C(=CC=CC=2)CC1O)C(C)(C)C)(C)(C)C.ClNC(=O)[O-].C([O:72][C:73]([C:75]1([NH:80][C:81]([CH:83]2[CH2:87][CH:86]([O:88][C:89]3[C:98]4[C:93](=[CH:94][C:95]([O:99][CH3:100])=[CH:96][CH:97]=4)[N:92]=[C:91]([C:101]4[CH:106]=[CH:105][CH:104]=[CH:103][CH:102]=4)[CH:90]=3)[CH2:85][N:84]2[C:107](=[O:127])[NH:108][CH:109]([C:114](=[O:126])[NH:115][CH:116]2[C:124]3[C:119](=[CH:120][CH:121]=[CH:122][CH:123]=3)CC2O)[C:110](C)([CH3:112])[CH3:111])=[O:82])[CH2:77][CH:76]1[CH:78]=[CH2:79])=[O:74])C>>[CH:124]1([CH2:116][NH:115][C:114]([C@@H:109]([NH:108][C:107]([N:84]2[CH2:85][C@H:86]([O:88][C:89]3[C:98]4[C:93](=[CH:94][C:95]([O:99][CH3:100])=[CH:96][CH:97]=4)[N:92]=[C:91]([C:101]4[CH:106]=[CH:105][CH:104]=[CH:103][CH:102]=4)[CH:90]=3)[CH2:87][C@H:83]2[C:81]([NH:80][C:75]2([C:73]([OH:74])=[O:72])[CH2:77][CH:76]2[CH:78]=[CH2:79])=[O:82])=[O:127])[CH:110]([CH3:111])[CH3:112])=[O:126])[CH2:119][CH2:120][CH2:121][CH2:122][CH2:123]1

Participants

7

Reactant 6

HCID 7965CyclohexylamineHCID 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 131727702HCID 131727702, compound

Procedure

N-(tert-butoxycarbonyl)-L-valine was attached to the resin as described for the preparation of compound 16 followed by reaction with cyclohexylamine 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+712.3.

Sources & evidence

ORD record
ord-a03c934ca5294b6597706b6cea0edd18
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

Loading…